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Carbohydrate Chemistry: Proven Synthetic Methods, Volume 1 [Kõva köide]

Edited by (National Institutes of Health, Bethesda, Maryland, USA)
  • Formaat: Hardback, 468 pages, kõrgus x laius: 234x156 mm, kaal: 1030 g, 5 Tables, black and white; 463 Illustrations, black and white
  • Sari: Carbohydrate Chemistry: Proven Synthetic Methods
  • Ilmumisaeg: 22-Sep-2011
  • Kirjastus: CRC Press Inc
  • ISBN-10: 1439866899
  • ISBN-13: 9781439866894
Teised raamatud teemal:
Carbohydrate Chemistry: Proven Synthetic Methods, Volume 1Suurem pilt
  • Formaat: Hardback, 468 pages, kõrgus x laius: 234x156 mm, kaal: 1030 g, 5 Tables, black and white; 463 Illustrations, black and white
  • Sari: Carbohydrate Chemistry: Proven Synthetic Methods
  • Ilmumisaeg: 22-Sep-2011
  • Kirjastus: CRC Press Inc
  • ISBN-10: 1439866899
  • ISBN-13: 9781439866894
Teised raamatud teemal:
Püsilink: https://www.kriso.ee/db/9781439866894.html
Märksõnad:
The series was started in order to provide a venue free of the junk that has been littering the literature on synthesizing carbohydrates--papers with little or no data, compounds someone made and never characterized, and the like. The synthetic methods described here have been thoroughly reproduced. Considering first synthetic methods, then synthetic intermediates, chemists from Europe and the Americas discuss such topics as using hypo-phosphorous acid in the radical chain deoxygenation of carbohydrates, a phosphoramidite approach to synthesizing sugar nucleotides, synthesizing theoglycodises and thioimidates from glycosyl, ethylene dithioacetals of common hexoses, and the functionalization of terminal positions of sucrose. Annotation ©2011 Book News, Inc., Portland, OR (booknews.com)

Long gone are the days when synthetic publications included parallel preparative experiments to document reproducibility of the experimental protocols and when journals required such documentation. The new Proven Synthetic Methods Series addresses concerns to chemists regarding irreproducibility of synthetic protocols, lack of characterization data for new compounds, and inflated yields reported in many chemical communications—trends that have recently become a serious problem.

Volume One of Carbohydrate Chemistry: Proven Synthetic Methods includes more detailed versions of protocols previously published for the synthesis of oligosaccharides, C-glycosyl compounds, sugar nucleotides, click chemistry, thioglycosides, and thioimidates, among others. The compilation of protocols covers both common and less frequently used synthetic methods as well as examples of syntheses of selected carbohydrate intermediates with general utility. The major focus of this book is devoted to the proper practice of state-of-the-art preparative procedures, including:

  • References to the starting materials used, reaction setup, work-up and isolation of products, followed by identification and proof of purity of the final material
  • General information regarding convenience of operation and comments on safety issues
  • Versatile and practically useful methods that have not received deserved, long-lasting recognition or that are difficult to access from their primary sources
  • Copies of 1D NMR spectra of compounds prepared, showing purity of materials readers can expect

Exploring carbohydrate chemistry from the academic points of view, the Carbohydrate Chemistry: Proven Synthetic Methods Series provides a compendium of preparatively useful procedures checked by chemists from independent research groups.

Arvustused

'The contributors are the best scientists in the field and the series editor is highly respected. The volumes will ... be of use to undergraduates involved in carbohydrate workshops.' Alexei Demchenko, Associate Professor of Chemistry and Biochemistry, Director of Graduate Studies, University of Missouri St. Louis.

This essential book series, focused on carbohydrate synthesis, starts with a dedication to Nobel Laureate Sir John W. Cornforth, who is credited with the first public criticism of what he pictured as pouring a large volume of unpurified sewage into the chemical literature.1 Unfortunately, this issue is not limited to the field of chemistry as many high profile cases of irreproducible experiments have led to alarms being set off even in the popular press.2 This series then serves as the much-needed water treatment plants places where the reader can be guaranteed a good clean reproducible experiment. at least now chemists with or without expertise in carbohydrates can count on finding reliable procedures to make sugar-based compounds at one scale a major achievement. Not only should current practitioners gain back time lost in attempts to properly reconstruct experimental procedures, but these procedures should also allow more creative scientists to contribute to this growing area.











Cornforth JW. Austr. J. Chem. 1993;46:157e70.





For example, see Unreliable research: trouble at the lab. Econ. October 19, 2013.

Nicola L.B. Pohl, Indiana University, Department of Chemistry, Bloomington, IN, USA, for Carbohydrate Research, http://dx.doi.org/10.1016/j.carres.2015.04.007. 'The contributors are the best scientists in the field and the series editor is highly respected. The volumes will ... be of use to undergraduates involved in carbohydrate workshops.' Alexei Demchenko, Associate Professor of Chemistry and Biochemistry, Director of Graduate Studies, University of Missouri St. Louis.

This essential book series, focused on carbohydrate synthesis, starts with a dedication to Nobel Laureate Sir John W. Cornforth, who is credited with the first public criticism of what he pictured as pouring a large volume of unpurified sewage into the chemical literature.1 Unfortunately, this issue is not limited to the field of chemistry as many high profile cases of irreproducible experiments have led to alarms being set off even in the popular press.2 This series then serves as the much-needed water treatment plants places where the reader can be guaranteed a good clean reproducible experiment. at least now chemists with or without expertise in carbohydrates can count on finding reliable procedures to make sugar-based compounds at one scale a major achievement. Not only should current practitioners gain back time lost in attempts to properly reconstruct experimental procedures, but these procedures should also allow more creative scientists to contribute to this growing area.











Cornforth JW. Austr. J. Chem. 1993;46:157e70.





For example, see Unreliable research: trouble at the lab. Econ. October 19, 2013.

Nicola L.B. Pohl, Indiana University, Department of Chemistry, Bloomington, IN, USA, for Carbohydrate Research, http://dx.doi.org/10.1016/j.carres.2015.04.007.

Foreword xiii
Derek Horton
Foreword xv
Paul Kosma
Foreword xvii
Bert Fraser-Reid
Introduction xix
Contributors xxiii
PART I Synthetic Methods
1 Acetolysis of 6-Deoxysugars Controlled by Armed---Disarmed Effect
3(8)
Emiliano Bedini
Luigi Cirillo
Ian Cumpstey
Michalangelo Parrilli
Experimental Methods
4(3)
General Methods
4(2)
Acetolysis Procedure
6(1)
Acknowledgments
7(3)
References
10(1)
2 NaH/Im2SO2-Mediated Preparation of Hex-2- and Hex-3-Enopyranoside Enol Ethers
11(16)
Emanuele Attolino
Giorgio Catelani
Felicia D'Andrea
Lorenzo Guazzelli
Marie-Christine Scherrmann
Experimental Methods
16(10)
General Methods
16(1)
Methyl 2,6-Di-O-Benzyl-4-Deoxy-3-O-Naphthylmethyl-β-D-threo-Hex-3-Enopyranoside(13)
16(1)
Methyl 2-O-Benzyl-4-Deoxy-3-O-p-Methoxybenzyl-6-O-Methoxymethyl-β-D-threo-Hex-3-Enopyranoside (15)
17(1)
3-Azidopropyl 2-Acetamido-3,6-Di-O-Benzyl-2,4-Dideoxy-β-D-threo-Hex-3-Enopyranosyl-(1 → 4)-2,3,6,-Tri-O-Benzyl-β-D-Glucopyranosyl-(1 → 2)-3,4-Di-O-Benzyl-α-L-Rhamnopyranoside (17)
17(1)
Methyl 3,4,6-Tri-O-Benzyl-2-Deoxy-β-D-threo-Hex-2-Enopyranoside (19)
18(1)
2-Deoxy-3,4-O-Isopropylidene-6-O-Trityl-β-D-threo-Hex-2-Enopyranosyl-(1 → 4)-2,3:5,6-Di-O-Isopropylidene-Aldehydo-D-Glucose Dimethyl Acetal (21)
Methyl 3,4-Di-O-Benzyl-2,6-Dideoxy-α-L-threo-Hex-2-Enopyranoside (23)
19(7)
References
26(1)
3 Enhancement of the Rate of Purdie Methylation by Me2S Catalysis
27(16)
Shujie Hou
Thomas Ziegler
Pavol Kovac
Experimental Methods
29(13)
General Methods
29(1)
General Procedure
29(1)
Methylation of Methyl 3-O-Benzyl-β-D-Galactopyranoside (1)
30(1)
Methylation of Methyl 6-O-Trityl-β-D-Galactopyranoside (3)
31(1)
Methylation of Methyl 6-O-Trityl-α-D-Glucopyranoside (5)
32(1)
Methylation of Methyl 2,3-Di-O-Benzyl-6-O-Benzoyl-β-D-Glucopyranoside (7)
33(2)
Acknowledgment
35(7)
References
42(1)
4 Synthesis of Oligosaccharides by Preactivation-Based Chemoselective Glycosylation of Thioglycosyl Donors
43(10)
Zhen Wang
Gilbert Wasonga
Benjamin M. Swarts
Xuefei Huangs
Experimental Methods
45(5)
General Methods
45(1)
P-Toluenesulfenyl Chloride (1)25
46(1)
P-Tolyl 6-O-(2,3,4-Tri-O-Benzoyl-6-O-Tert-Butyldiphenylsilyl-β-D-Glucopyranosyl)-2,3,4-Tri-O-Benzyl-1-Thio-β-D-Glucopyranoside (4)
46(1)
Methyl-2-O-Benzoyl-3-O-Benzyl-4-O-tert-Butyldimethylsilyl)-6-0-p-Methoxybenzyl-β-D-Glucopyranosyl-(1 → 3)-4,6-O-Benzylidene-2-Deoxy-2-N-Phthalimido-β-D-Galactopyranosyl-(1 → 4)-2,3-Di-O-Benzyl-6-O-p-Methoxybenzyl-β-D-Glucopyranoside (8)
47(1)
Acknowledgment
48(2)
References
50(3)
5 The Use of Hypophosphorous Acid in Radical Chain Deoxygenation of Carbohydrates
53(14)
Karsten Krohn
Ivan Shuklov
Ishtiaq Ahmed
Alice Voss
Experimental Methods
56(7)
General Method
56(1)
Methyl 2,3-O-Isopropylidene-4-O-[ (Methylsulfanyl)thiocarbonyl]-6-O-Triphenylmethyl-α-D-Mannopyranoside (2)
57(1)
Methyl 4-Deoxy-2,3-O-Isopropylidene-6-O-Triphenylmethyl-α-D-Lyxo-Hexopyranoside (3)
57(1)
1,2:5,6-Di-O-Isopropylidene-3-O-[ (Methylsulfanyl)thiocarbonyl]-α-D-Glucofuranose (5)
58(1)
3-Deoxy-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (6)
58(1)
1,2:4,5-Di-O-Isopropylidene-3-O-[ (Methylsulfanyl)thiocarbonyl]-β-D-Fructopyranose (8)
58(1)
3-Deoxy-1,2:4,5-Di-0-Isopropylidene-β-D-Erythro-Hex-2-Ulopyranose (9)
59(1)
1,6-Anhydro 4-O-Benzyl-2-Deoxy-2-C-Methyl-3-O-[ (Methylsulfanyl)thiocarbonyl]-β-D-Glucopyranose (11)
59(1)
1,6-Anhydro 4-O-Benzyl-2,3-Dideoxy-2-C-Methyl-β-D-Ribo-Hexopyranose (12)
59(4)
References
63(4)
6 Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator for Thioglycosides
67(6)
Jeroen D.C. Codee
Thomas J. Boltje
Gijsbert A. van der Marel
Experimental Methods
68(2)
General Methods
68(1)
Methyl (4-O-Acetyl-2,3-Di-O-β-D-Mannopyranosyl)-(1 → 6)-(Methyl 2,3,4-Tri-O-Benzyl-α-D-Glucopyranosid)uronate (6)
69(1)
Acknowledgments
70(1)
References
71(2)
7 Preparation of Glycosyl Chlorides from Glycopyranoses/Glycopyranoses under Mild Conditions
73(10)
Chih-Wei Chang
Chin-Sheng Chao
Chang-Ching Lin
Kwok-Kong T. Mong
Introduction
73(2)
General TCT/DMF Chlorination Protocols
75(1)
Experimental Methods
75(6)
General Methods
75(1)
TCT/DMF Chlorination Protocol A for Preparation of Glycosyl Chlorides 1a and 2a
76(1)
TCT/DMF Chlorination Protocol B for Preparation of Glycosyl Chlorides 3a and 4a
76(1)
2,3,4,6-Tetra-O-Acetyl-α-D-Glucopyranosyl Chloride (1a)
76(1)
2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyl Chloride (2a)
77(1)
2,3,4,6-Tetra-O-Benzyl-α-D-Galactopyranosyl Chloride (3a)
77(1)
2,3:5,6-Di-O-Isopropylidene-α-D-Mannofuranosyl Chloride (4a)
77(1)
Acknowledgment
78(3)
References
81(2)
8 C-Glycosylation Starting from Unprotected O-Glycosides
83(8)
Barbara La Ferla
Laura Cipolla
Wouter Hogendorf
Francesco Nicotra
Experimental Methods
84(2)
General Methods
84(1)
3-(α-D-Galactopyranosyl)prop-l-Ene (2)
85(1)
Bicyclic Iodoethers (3)
85(1)
Methyl (2R)-2-Acetamido-3-(α-D-Galactopyranosylpropylthio) propanoate (4)
85(1)
Acknowledgments
86(3)
References
89(2)
9 Palladium-Catalyzed Sonogashira Coupling on p-lodophenyl α-D-Mannopyranoside
91(4)
Tze Chieh Shiao
Jacques Rodrigue
Mohamed Touaibia
Experimental Methods
92(1)
General Methods
92(1)
3-[ 4-(2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyloxy)phenyl]prop-2-Yn-l-ol (2)
92(1)
Acknowledgments
93(1)
References
94(1)
10 Synthesis by "Click Chemistry" of an α-D-Mannopyranoside Having a 1,4-Disubstituted Triazole as Aglycone
95(4)
Tze Chieh Shiao
Denis Giguere
Mohamed Touaibia
Experimental Methods
96(1)
General Methods
96(1)
Methyl2-{[ 4-(2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranosyloxy)methyl]-1H-l,2,3-Triazol-l-yl]}Acetate (2)
96(1)
Acknowledgments
97(1)
References
98(1)
11 Synthesis of Methyl Glycuronates by Chemo-and Regioselective TEMPO/BAIB-Oxidation
99(8)
Marthe T.C. Walvoort
Deepak Sail
Gijsbert A. van der Marel
Jeroen D.C. Codee
Experimental Methods
101(2)
General Methods
101(1)
Phenyl3-O-Benzoyl-2-Deoxy-2-Phthalimido-1-Thio-β-D- Glucopyranosyluronic Acid (2)
102(1)
Methyl(Phenyl3-O-Benzoyl-2-Deoxy-2-Phthalimido-1-Thio-β-D-Glucopyranoside) Uronate (3)
102(1)
Acknowledgments
103(1)
References
104(3)
12 Synthesis of Sugar Nucleotides: A Phosphoramidite Approach
107(6)
Henrik Gold
Karine Descroix
Jeroen D.C. Codee
Gijsbert A. van der Marel
Experimental Methods
109(3)
General Methods
109(1)
Uridine5'-(2-Acetamido-2-Deoxy-α-D-GlucopyranosylDiphosphate)Disodium Salt(5)
109(3)
References
112(1)
13 Conversion of N-2,2,2-Trichloroethoxycarbonyl-Protected 2-Aminoglycosides into N-Alkylated 2,3-N, O-Carbonyl Glycosides
113(16)
Thomas Honer
Siegfried Forster
Thomas Ziegler
Experimental Methods
115(12)
General Methods
115(1)
General Procedure
115(1)
2-Trimethylsilylethyl 4,6-O-Benzylidene-2-Deoxy-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Glucopyranoside (1)
115(1)
2-Trimethylsilylethyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, O-Carbonyl-2-Deoxy-β-D-Glucopyranoside (2)
116(1)
Phenyl 4,6-O-Benzylidene-2-Deoxy-1-Thio-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Glucopyranoside (3)
116(1)
Phenyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, O-Carbonyl-2- Deoxy-1-Thio-β-D-Glucopyranoside (4)
117(1)
Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(4-Nitrobenzyl)-1-Thio-β-D-Glucopyranoside (5)
117(1)
Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(4-Methoxybenzyl)-1-Thio-β-D-Glucopyranoside (6)
117(1)
Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(Prop-2-Enyl)-1-Thio-β-D-Glucopyranoside (7)
118(1)
Phenyl 2-Amino-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-2-N-(Prop-2-Ynyl)-1-Thio-β-D-Glucopyranoside (8)
118(1)
Phenyl 4,6-O-Benzylidene-2-Deoxy-1-Thio-2-(2,2,2-Trichlorethoxycarbamido)-β-D-Galactopyranoside (9)
118(1)
Phenyl 2-Amino-2-N-Benzyl-4,6-O-Benzylidene-2,3-N, o-Carbonyl-2-Deoxy-l-Thio-β-D-Galactopyranoside (10)
119(8)
References
127(2)
14 TIBAL-lnduced Rearrangement: Synthesis of gem-Difluorocarbagalactose
129(8)
Joao Sardinha
Amelia Pilar Rauter
Matthieu Sollogoub
Yves Bleriot
Experimental Methods
131(4)
General Methods
131(1)
Rearrangement of 1 into 2,3,4-Tri-O-Benzyl-6,7,8-Trideoxy-5a-Difluoro-5a-Carba-α-D-Galacto-Oct-6-Ynopyranose (4) and 2,3,4-Tri-O-Benzyl-6,7,8-Trideoxy-5a-Difluoro-5a-Carba-β-D-Galacto-Oct-6-Ynopyranose (5)
132(1)
Acknowledgment
132(3)
References
135(2)
15 Pyranose-Fused Butenolides: An Expedient Preparation from Furanose Synthons
137(22)
Nuno M. Xavier
Sebastian Kopitzki
Amelia Pilar Rauter
Experimental Methods
140(17)
General Methods
140(1)
1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranosid-3-Ulose (1)
141(1)
3-Deoxy-3-C-[ (Z)-(Ethoxycarbonyl)methylene]-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (2) and 3-Deoxy-3-C-[ (E)-(Ethoxycarbonyl)methylene]-1,2:5,6-Di-O-Isopropylidene-α-D-Ribo-Hexofuranose (3)
141(1)
3-C-(Carboxymethylene)-3-Deoxy-D-Ribo-Hexopyranose-3', 2-Lactone (4)
141(1)
3-Deoxy-3-C-[ (Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Ribo-Hexofuranose (5)
142(1)
3-Deoxy-3-C-[ (Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-6-O-Pivaloyl-α-D-Ribo-Hexofuranose (6) and 3-Deoxy-3-C-[ (Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-5,6-Di-O-Pivaloyl-α-D-Ribo-Hexofuranose (7)
142(1)
3-C-(Carboxymethylene)-3-Deoxy-6-O-Pivaloyl-D-Ribo-Hexopyranose-3',2-Lactone (8)
143(1)
1,4,6-Tri-O-Acetyl-3-C-(Carboxymethylene)-3-Deoxy-D-Ribo-Hexopyranose-3',2-Lactone (9)
143(1)
5-O-Tert-Butyldimethylsilyl-1,2-O-Isopopylidene-α-D-Erythro-Pentofuranos-3-Ulose (10)
144(1)
5-0-Tert-Butyldimethylsily1-3-Deoxy-3-C-[ (Z)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Erythro-Pentofuranose (11) and 5-O-Tert-Butyldimethylsilyl-3-Deoxy-3-C-[ (E)-(Ethoxycarbonyl)methylene]-1,2-O-Isopropylidene-α-D-Erythro-Pentofuranose (12)
144(1)
3-C-(Carboxymethylene)-3-Deoxy-D-Erythro-Pentopyranose-3',2-Lactone (13)
145(1)
Acknowledgment
145(12)
References
157(2)
16 Glycal Dimerization with High Diastereoselectivity
159(8)
Andreas H. Franz
Paul H. Gross
Katja Michael
Experimental Methods
160(4)
General Methods
160(1)
General Method for the Dimerization of Glycals
161(1)
1,3,4,6-Tetra-O-Acetyl-2-C-(4,6-Di-O-Acetyl-2,3-Dideoxy-α-D-Erythro-Hex-2-Enopyranosyl)-2-Deoxy-α/β-D-Glucopyranose (2a, 2b)
162(2)
Acknowledgments
164(2)
References
166(1)
17 Regioselective Debenzylation of C-Glycosylpropene
167(8)
Laura Cipolla
Barbara La Ferla
Amelia Pilar Rauter
Francesco Nicotra
Experimental Methods
168(5)
General Methods
168(1)
General Procedure for Iodocyclization
169(1)
β-Elimination
169(1)
3-C-(3,4,6-Tri-O-Benzyl-α-D-Glucopyranosyl)Prop-1-Ene (3)
169(1)
3-C-(3,4,6-Tri-O-Benzyl-α-D-Fructofuranosyl)Prop-1-Ene (6)
170(1)
Acknowledgment
171(2)
References
173(2)
18 Synthesis of Azido-Functionalized Carbohydrates for the Design of Glycoconjugates
175(6)
Samy Cecioni
Mehdi Almant
Jean-Pierre Praly
Sebastien Vidal
Experimental Methods
176(2)
General Methods
176(1)
General Procedure for Glycosylation
177(1)
1-Azido-3,6-Dioxaoct-8-yl 2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranoside 2
177(1)
1-Azido-3,6-Dioxaoct-8-yl 2,3,6,2',3',4',6'-Hepta-O-Acetyl-β-Lactoside 4
178(1)
Acknowledgments
178(2)
References
180(1)
19 Synthesis of Thioglycosides and Thioimidates from Glycosyl Halides
181(6)
Archana R. Parameswar
Daniel Mueller
Lin Liu
Cristina De Meo
Alexei V. Demchenko
Experimental Methods
182(1)
1,3-Benzoxazol-2-yl 2,3,4,6-Tetra-O-Acetyl-l-Thio-β-D-Glucopyranoside (3)
182(1)
Methyl (Phenyl 5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-2-Thio-D-Glycero-α-D-Galato-Non-2-Ulopyranosid)onate (6)
183(1)
Acknowledgments
183(2)
References
185(2)
20 Synthesis of Thioglycosides and Thioimidates from Peracetates
187(12)
Archana R. Parameswar
Akihiro Imamura
Alexei V. Demchenko
Experimental Methods
189(6)
General Methods
189(1)
Phenyl 2,3.4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (2)
189(1)
4,5-Dihydro-1,3-Thiazol-2-yl 2,3,4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (3)
190(1)
Ethyl 2,3,4,6-Tetra-O-Acetyl-1-Thio-β-D-Glucopyranoside (4)
190(1)
P-Tolyl 2,3.4.6-Telra-O-Acetyl-1-Thio-β-D-Glucopyranoside (5)
191(1)
Acknowledgment
191(4)
References
195(4)
PART II Synthetic Intermediates
21 2-Acetamido-4,6-O-BenzyIidene-2-Deoxy-D-GIucopyranose
199(6)
Sergey S. Pertel
Sergey A. Gunchak
Elena S. Kakayan
Vasily Ya. Chirva
Sebastien Vidal
Experimental Methods
200(3)
General Methods
200(1)
2-Acetamido-4,6-O-Benzylidene-2-Deoxy-D-Glucopyranose (2)
200(2)
Acknowledgment
202(1)
References
203(2)
22 Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose and 2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose
205(8)
Rafael Ojeda
Jose Luis de Paz
Ricardo Lucas
Niels Reichardt
Lin Liu
Manuel Martin-Lomas
Experimental Methods
206(5)
General Methods
206(1)
Preparation of Trifluoromethanesulfonyl Azide (TfN3) Solution
207(1)
1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-D-Glucopyranose (2)
207(1)
2-Azido-4,6-O-Benzylidene-2-Deoxy-α,β-D-Glucopyranose (3)
208(3)
References
211(2)
23 An Easy Access to 2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose and 2,3,6-Tri-O-Benzyl-D-Glucopyranose
213(8)
Ian Cumpstey
Riccardo Cribiu
Lorenzo Guazzelli
Experimental Methods
214(6)
General Methods
214(1)
Benzyl 2,3,4,6-Tetra-O-Benzyl-β-D-Galactopyranosyl-(1 → 4)-2,3,6-Tri-O-Benzyl-β-D-Glucopyranoside (II)
215(1)
2,3,4,6-Tetra-O-Benzyl-D-Galactopyranose (IV), 2,3,6-Tri-O-Benzyl-D-Glucopyranose (V) and 1-O-Acetyl-2,3,4,6-Tetra-O-Benzyl-β-D-Galactopyranose (III)
216(4)
References
220(1)
24 Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl-β-Cellobioside
221(10)
Deepak Sail
Paula Correia da Silva
Pavol Kovaac
Experimental Methods
222(8)
General Methods
222(1)
Benzyl 2,3,6,2',3'-Penta-O-Benzyl-4',6'-O-Benzylidene-α-Cellobioside (2A) and Benzyl 2,3,6,2',3'-Penta-O-Benzyl-4',6'-O-Benzylidene-β-Cellobioside (2B)
223(1)
Benzyl 2,3,6,2',3',6'-Hexa-O-Benzyl-β-Cellobioside (3) and Benzyl 2,3,6,2',3',4'-Hexa-O-Benzyl-β-Cellobioside (9)
224(1)
Acknowledgment
225(5)
References
230(1)
25 One-Step Syntheses of 1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose and 1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose
231(8)
Carla Marino
Lucia Gandolfi-Donadio
Carola Gallo Rodriguez
Yu Bai
Rosa M. de Lederkremer
Experimental Methods
233(2)
General Methods
233(1)
1,2,3,5,6-Penta-O-Benzoyl-α,β-D-Galactofuranose (1α and 1β)
233(1)
1,2,3,5-Tetra-O-Benzoyl-α,β-D-Arabinofuranose (2αβ), 1,2,3,5-Tetra-O-Benzoyl-α-D-Arabinofuranose (2α) and 1,2,3,4-Tetra-O-Benzoyl-α-D-Arabinopyranose (3)
234(1)
Acknowledgments
235(2)
References
237(2)
26 Stereoselective Synthesis of α-C-Sialyl Compounds
239(6)
Jin-Hwan Kim
Fei Huang
Sayaka Masuko
Deepak Sail
Robert J. Linhardt
Introduction
239(1)
Experimental Methods
240(2)
General Methods
240(1)
SmI2 Mediated C-Sialylation: 4,4-Dimethyl-l-[ Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-D-Glycera-α-D-Galacto-Non-2-Ulopyranosyl)onate]cyclohexanol (3)
240(2)
References
242(3)
27 Synthesis of O-Acetylated N-Acetylneuraminic Acid Glycal
245(6)
Nadezhda Y. Kulikova
Anna M. Shpirt
A. Chinarev
Leonid O. Kononov
Experimental Methods
246(4)
General Methods
246(1)
Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-β-D-Glycero-D-Galacto-Non-2-Ulopyranosyl)onate Chloride (2)
246(3)
Methyl (5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-2,6-Anhydro-D-Glycero-D-Galacto-Non-2-Enopyranos)onate (3)
249(1)
Acknowledgment
250(1)
References
250(1)
28 Substituted Benzyl Glycosides of N-Acetylneuraminic Acid
251(8)
A. Chinarev
A.B. Tuzikov
A.I. Zinin
N.V. Bovin
Experimental Methods
253(4)
General Methods
253(1)
Methyl {4-[ (Tert-Butyloxycarbonyl)glycylarmido]benzyl 5-Acetamido-4,7,8,9-Tetra-O-Acetyl-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosid}onate (3)
253(3)
4-[ (Tert-Butyloxycarbonyl)glycylamido]benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (5)
256(1)
4-(Glycylamido)benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (6)
256(1)
4-[ (4-Nitrophenoxy)adipoylglycylamido]benzyl 5-Acetamido-3,5-Dideoxy-D-Glycero-D-Galacto-Non-2-Ulopyranosidonic Acid (8)
257(1)
Acknowledgment
257(1)
References
257(2)
29 Synthesis of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related to 1-Deoxynojirimycin
259(10)
Vincent Chagnault
Philippe Compain
Olivier R. Martin
Jean-Bernard Behr
Introduction
259(2)
Experimental Methods
261(6)
General Methods
261(1)
1,5-Di-(1/2-Benzotriazolyl)-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (4)
261(1)
2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-N-Benzyl-1,5-Dideoxy-1,5-Iminoxylitol (5)
262(1)
Meso-(1R,5S)-, Meso-(1S,5R), and Rac-(1R,5R)-2,3,4-Tri-O-Acetyl-1,5-Di-C-Allyl-1,5-Dideoxy-1,5-Iminoxylitol (6a, 6b, and 6c)
262(1)
Acknowledgment
263(4)
References
267(2)
30 Synthesis of 1,6-Anhydro 2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose
269(6)
Sujit K. Sarkar
Ambar K. Choudhury
Jan Hirsch
Nirmolendu Roy
Experimental Methods
270(4)
General Methods
270(1)
6-O-Benzyl-1,2:3,4-Di-O-Isopropylidene-α-D-Galactopyranose (2)
270(1)
Methyl 2,3,5-Tri-O-Benzoyl-6-O-Benzyl-β-D-Galactofuranoside (4)
270(1)
1,6-Anhydro-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranose (5)
271(1)
1,6-Anhydro-α-D-Galactofuranose (6)
271(1)
1,6-Anhydro-2,3,5-Tri-O-Acetyl-α-D-Galactofuranose (7)
271(1)
Acknowledgment
271(3)
References
274(1)
31 Synthesis of Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside
275(4)
Yoann M. Chabre
Tze Chieh Shiao
Sebastien Vidal
Rene Roy
Experimental Methods
276(1)
General Methods
276(1)
Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl-α-D-Mannopyranoside (2)
276(1)
Acknowledgments
277(1)
References
278(1)
32 Synthesis of 3-C-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl) prop-1-Ene
279(6)
Subhash Rauthu
Tze Chieh Shiao
Dominique Lafont
Rene Roy
Experimental Methods
280(1)
General Methods
280(1)
2,3,4,6-Tetra-O-Acetyl-α-D-Galactopyranosyl Bromide (1)
280(1)
3-C-(2,3.4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)Prop-l-Ene (2)
281(1)
Acknowledgments
281(1)
References
282(3)
33 Synthesis of (E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl) but-2-Enoate by Cross-Metathesis Reaction
285(4)
Denis Giguere
Jacques Rodrigue
David Goyard
Rene Roy
Experimental Methods
286(2)
General Methods
286(1)
(E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)but-2- Enoate (2)
286(1)
Acknowledgment
287(1)
References
288(1)
34 Preparation of O-β-D-Galactopyranosyl-hydroxylamine
289(6)
Tze Chieh Shiao
Alex Papadopoulos
Olivier Renaudet
Rene Roy
Experimental Methods
290(1)
General Methods
290(1)
O-(2,3,4,6-Tetra-O-Acetyl-β-D-Galactopyranosyl)-N-Hydroxysuccinimide (2)
290(1)
O-β-D-Galactopyranosylhydroxylamine (3)
291(1)
Acknowledgments
291(2)
References
293(2)
35 Synthesis of 2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol and Its Conversion into a Hex-3-Enopyranosid-2-Ulose Analogue of Levoglucosenone
295(8)
Veronica E. Manzano
Evangelina Repetto
Maria Laura Uhrig
Marek Barath
Oscar Varela
Experimental Methods
296(2)
General Methods
296(1)
2,3,4,6-Tetra-O-Acetyl-1,5-Anhydro-D-Lyxo-Hex-1-Enitol (3)
297(1)
Benzyl 3,4-Dideoxy-α-D-Glycero-Hex-3-Enopyranosid-2-Ulose (4)
298(1)
Acknowledgments
298(3)
References
301(2)
36 Efficient Synthesis of Methyl(Allyl 4-O-Acyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid) uronates from D-Galacturonic Acid
303(24)
Alice Voss
Navid Nemati
Hmayak Poghosyan
Hans-Ulrich Endress
Andreas Krause
Christian Vogel
Experimental Methods
306(20)
General Methods
306(1)
1,2,3,4-Tetra-O-Acetyl-α-D-Galactopyranuronic Acid (11)
307(1)
Methyl 1,2,3,4-Tetra-O-Acetyl-α-D-Galactopyranuronate (12)
308(1)
Methyl 2,3,4-Tri-O-Acetyl-α-D-Galactopyranosyluronate Bromide (13)
308(1)
Methyl (Allyl 2,3,4-Tri-O-Acetyl-β-D-Galactopyranosid)uronate (14)
308(1)
Methyl (Allyl β-D-Galactopyranosid)uronate (19)
309(1)
Regioselective Ring Opening in Orthoester Structures 20 and 21
309(1)
Methyl (Allyl 4-O-Acetyl-β-D-Galactopyranosid)uronate (22)
309(1)
Methyl (Allyl 4-O-Benzoyl-β-D-Galactopyranosid)uronate (23)
310(1)
Benzylation of Compounds 22 and 23
310(1)
Methyl (Allyl 4-O-Acetyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (1)
310(1)
Methyl (Allyl 4-O-Benzoyl-2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (2)
310(1)
Methyl (Allyl 2,3-Di-O-Benzyl-β-D-Galactopyranosid)uronate (5)
311(15)
References
326(1)
37 Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate
327(14)
Ambar K. Choudhury
Dirk Michalik
Andreas Gottwald
Nirmolendu Roy
Experimental Methods
329(10)
General Methods
329(1)
Tert-Butyl 1,2:3,4-Di-O-Isopropylidene-α-D-Galactopyranuronate (2)
330(1)
Methyl (Methyl α,β-D-Galactofuranosid)uronate (3)
330(1)
Methyl (Methyl α-D-Galactofuranosid)uronate (3α)
330(1)
Methyl (Methyl β-D-Galactofuranosid)uronate (3β)
330(1)
Methyl (Methyl 2,3,5-Tri-O-Benzoyl-α,β-D-Galactofuranosid)uronate (4)
330(1)
Methyl (Methyl 2,3,5-Tri-O-Benzoyl-α-D-Galactofuranosid)uronate (4α)
331(1)
Methyl (Methyl 2,3,5-Tri-O-Benzoyl-β-D-Galactofuranosid)uronate (4β)
331(1)
Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-α,β-D-Galactofuranuronate (5)
331(1)
Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-α-D-Galactofuranuronate (5α)
331(1)
Methyl 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-β-D-Galactofuranuronate (5β)
332(1)
Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α,β-D-Galactofuranosid)uronate (6)
332(1)
Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Galactofuranosid)uronate (6α)
332(1)
Methyl (Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-β-D-Galactofuranosid)uronate (6β)
332(7)
References
339(2)
38 P-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside: A Useful Thioglycoside Building Block In The Synthesis Of Oligoarabinofuranosides
341(8)
Maju Joe
Yu Bai
Lucia Gandolfi-Donadio
Todd L. Lowary
Experimental Methods
342(2)
General Methods
342(1)
P-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio-α-D-Arabinofuranoside
343(1)
Waste Disposal Information
344(1)
Acknowledgments
344(3)
References
347(2)
39 Ethylene Dithioacetals of Common Hexoses
349(6)
Rui C. Pinto
Marta M. Andrade
Cecile Ouairy
Maria Teresa Barros
Experimental Methods
350(4)
General Methods
350(1)
General Procedure
350(1)
D-Galactose Ethylene Dithioacetal (1)
350(1)
D-Glucose Ethylene Dithioacetal (2)
350(1)
D-Mannose Ethylene Dithioacetal (3)
351(3)
References
354(1)
40 Preparation of 2,6-Anhydro-Aldose Tosylhydrazones
355(12)
Marietta Toth
Laszlo Somsak
David Goyard
Experimental Methods
357(2)
General Methods
357(1)
General Procedure
357(1)
2,6-Anhydro-3,4,5,7-Tetra-O-Benzoyl-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2a)
358(1)
3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2b)
358(1)
3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-D-Glycera-L-Manno-Heptose Tosylhydrazone (2c)
358(1)
4,5,7-Tri-O-Acetyl-2,6-Anhydro-3-Deoxy-3-Phthalimido-D-Glycero-D-Gulo-Heptose Tosylhydrazone (2d)
359(1)
3,4,5-Tri-O-Acetyl-2,6-Anhydro-D-Manno-Hexose Tosylhydrazone (2e)
359(1)
Acknowledgments
359(6)
References
365(2)
41 Preparation of Exo-Glycals from (C-Glycopyranosyl) formaldehyde Tosylhydrazones
367(10)
Marietta Toth
Sandor Kun
Laszlo Somsak
David Goyard
Experimental Methods
369(2)
General Methods
369(1)
General Procedure
369(1)
2,6-Anhydro-3,4,5,7-Tetra-O-Benzoyl-1-Deoxy-D-Gluco-Hept-1-Enitol (2a)
370(1)
3,4,5,7-Tetra-O-Acetyl-2,6-Anhydro-1-Deoxy-D-Galacto-Hept-1-Enitol (2b)
370(1)
4,5,7-Tri-O-Acetyl-2,6-Anhydro-1,3-Dideoxy-3-Phthalimido-D-Gluco-Hept-1-Enitol (2c)
370(1)
3,4,5-Tri-O-Acetyl-2,6-Anhydro-1-Deoxy-D-Arabino-Hex-1-Enitol (2d)
370(1)
Acknowledgments
371(4)
References
375(2)
42 Synthsis of O-(6-Deoxy-α-and β-L-Galactopyranosyl) Hydroxylamines (α-and β-L-Fucopyranosyl-hydroxylamines)
377(10)
Isabelle Bossu
Barbara Richichi
Pascal Dumy
Olivier Renaudet
Experimental Methods
378(3)
General Methods
378(1)
O-(2,3,4-Tri-O-Acetyl-6-Deoxy-α-L-Galactopyranosyl)-N-Hydroxyphthalimide (2) and O-(2,3,4-Tri-O-Acetyl-6-Deoxy-β-L-Galactopyranosyl)-N-Hydroxyphthalimide (3)
379(1)
O-(6-Deoxy-α-L-Galactopyranosyl)Hydroxylamine(O-α-L-Fucopyranosylhydroxylamine) (4)
380(1)
O-(6-Deoxy-β-L-Galactopyranosyl)Hydroxylamine(O-β-L-Fucopyranosylhydroxylamine) (5)
380(1)
Acknowledgments
381(4)
References
385(2)
43 Functionalization of Terminal Positions of Sucrose---Part I: Synthesis of 2,3,3',4,4'-Penta-O-Benzylsucrose and Differentiation of the Terminal Positions (1,6,6')
387(26)
Mateusz Mach
A. Zawisza
B. Lewandowski
S. Jarosz
Experimental Methods
389(22)
General Methods
389(1)
1',6,6'-Tri-O-Tritylsucrose (2)
390(1)
2,3,3',4,4'-Penta-O-Benzyl-1',6,6'-Tri-O-TrityIsucrose (3)
391(1)
2,3,3',4,4'-Penta-O-Benzylsucrose (4)
391(1)
2,3,3',4,4'-Penta-O-Benzyl-6,6'-Di-O-p-Nitrobenzoylsucrose (5)
392(1)
2,3,3'4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6,6'-Di-O-p-Nitrobenzoylsucrose (6)
392(1)
2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethylsucrose (7)
392(1)
2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6'-O-Tert-Butyldiphenylsilylsucrose (8)
393(1)
Carbohydradte Chemistry: Proven Synthetic Methods
1'-O-Benzyloxymethyl-6,6'-Di-O-Tert-Butyldiphenylsilyl-2,3,3'4,4'-Penta-O-Benzylsucrose (9)
393(1)
2,3,3',4,4'-Penta-O-Benzyl-1'-O-Benzyloxymethyl-6-O-Tert-Butyldiphenylsilylsucrose (10)
394(17)
References
411(2)
44 Functionalization of Terminal Positions of Sucrose---Part II: Preparation of 1',2,3,3',4,4'-Hexa-O-Benzylsucrose and 6,6'-Bis-O-(2-Hydroxyethyl)-1',2,3,3',4,4'-Hexa-O-Benzylsucrose
413(18)
B. Lewandowski
A. Listkowski
K. Petrova
S. Jarosz
Experimental Methods
414(16)
General Methods
414(2)
6,6'-Di-O-Tritylsucrose (1)
416(1)
1',2,3,3',4,4'-Hexa-O-Acetyl-6,6'-Di-O-Tritylsucrose (1A)
417(1)
1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Di-O-Tritylsucrose (2)
417(1)
1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Dichloro-6,6'-Dideoxysucrose (3A)
418(1)
6,6'-Di-O-Acetyl-1',2,3,3',4,4'-Hexa-O-Benzylsucrose (4)
418(1)
1',2,3,3',4,4'-Hexa-O-Benzylsucrose (5)
419(1)
6,6'-Di-O-Allyl-1',2,3,3',4,4'-Hexa-O-Benzylsucrose (6)
419(1)
1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Bis-(O-Tert-Butoxycarbonylmethylsucrose (7)
420(1)
1',2,3,3',4,4'-Hexa-O-Benzyl-6,6'-Bis-(O-2-Hydroxyethyl) Sucrose (8)
420(10)
References
430(1)
Index 431
Series editor Pavol Ková, Ph.D., Dr. h.c., with more than 40 years of experience in carbohydrate chemistry and more than 270 papers published in refereed scientific journals or books, is a strong promoter of good laboratory practices and a vocal critic of the publication of experimental chemistry lacking data that allows reproducibility. He obtained an MSc in Chemistry at Slovak Technical University in Bratislava (Slovakia) and a PhD in Organic Chemistry at the Institute of Chemistry, Slovak Academy of Sciences, Bratislava. After postdoctoral training at the Department of Biochemistry, Purdue University, Lafayette, Indiana (R. L. Whistler, advisor), he returned to the Institute of Chemistry and formed a group of synthetic carbohydrate chemists, active mainly in oligosaccharide chemistry, which put the Institute on the map for quality synthetic carbohydrate chemistry.

After relocating to the United States in 1981, he first worked at Bachem, Inc., Torrance, California, where he established a laboratory for production of oligonucleotides for the automated synthesis of DNA. In 1983 he joined the National Institutes of Health, where he is currently one of the Principal Investigators and Chief of the Section on Carbohydrates (NIDDK, Laboratory of Bioorganic Chemistry), the worlds oldest research group continuously working on chemistry, biochemistry, and immunology of carbohydrates, originally established by Americas greatest carbohydrate chemist, Claude S. Hudson. Dr. Kovás main interest is in development of conjugate vaccines for bacterial diseases from synthetic carbohydrate antigens.