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E-raamat: Carbohydrate Chemistry: Proven Synthetic Methods, Volume 2

Edited by (Leiden University, The Netherlands), Edited by (Leiden University, The Netherlands)
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The second volume in the series Carbohydrate Chemistry: Proven Synthetic Methods, Volume 2 offers a collection of synthetic procedures valuable to the practice of synthetic carbohydrate chemistry. The series takes an important and unique approach in that all described procedures have been independently verified as reliable and reproducible. With editors and contributors who are highly respected scientists in the field, this book provides a widely useful reference for both researchers and students, exploring carbohydrate chemistry from both academic and industrial points of view.

The book begins with an introductory section that offers tricks and tips collected by the series editor from many years of experience working in carbohydrate laboratories. The subsequent chapters present detailed protocols on both specific synthetic transformations and the preparation of common synthetic intermediates, with figures to aid in comprehension. Procedures are described for regioselective benzylidene ring opening reactions, oxidation reactions to provide uronic acids, stereoselective alpha-glucosylation reactions, and more. Protocols for synthetic intermediates of general utility include 3,4,6-tri-O-acetyl-d-galactal, phenyl 4,6-O-benzylidene-1-thio--d-mannopyranoside, 1,2-anhydro-3,4,6-tri-O-benzyl--d-mannopyranoside, and methyl N-acetylneuraminic acid, among many others.

Each chapter presents in-depth experimental descriptions for the reported procedures, including reaction setup, reaction conditions, work-up procedures, and purification protocols. The chapters also provide detailed characterization of all products and intermediates as well as copies of the 1H NMR and 13C NMR of the described products and intermediates to indicate the purity of the obtained materials and to serve as a valuable reference for future practitioners.

This book provides an important starting point to reliably access synthetic carbohydrate materials and as such offers a valuable resource for the synthetic organic chemistry community. Through the streamlined access of well-defined products it provides a thrust to the rapidly growing field of chemical glycobiology.

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.

In Lieu of an Introduction xi
Series Editor xxvii
Book Editors xxix
Contributors xxxi
Section I Synthetic Methods
Chapter 1 Highly Stereoselective 1,2-cis-Glycosylations Employing the C-2 (S)-(Phenylthiomethyl)benzyl Ether as a Chiral Auxiliary
3(6)
Thomas J. Boltje
Randy Benedict
Geert-Jan Boons
Chapter 2 Regioselective Reductive Openings of 4,6-O-Benzylidene-Type Acetals Using LiAlH4-AlCl3
9(12)
Mihaly Herczeg
Laszlo Lazar
Markus Ohlin
Aniko Borbas
Chapter 3 A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids in Carbohydrate Synthesis
21(12)
Zhaojun Yin
Steven Dulaney
Gopinath Tiruchinapally
Bo Yang
Guitao Wang
Xuefei Huang
Chapter 4 Ultrasonic Energy Promoted Allylation to Generate 1-C-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)prop-2-ene
33(6)
Mark Farrell
Ciaran O'Reilly
Dilip V. Jarikote
Paul V. Murphy
Jani Rahkila
Chapter 5 Synthesis of a Multivalent Glycocyclopeptide Using Oxime Ligation
39(8)
Isabelle Bossu
Baptiste Thomas
Rene Roy
Pascal Dumy
Olivier Renaudet
Chapter 6 Reductive Amination Methodology for Synthesis of Primary Amines from Unprotected Synthons
47(6)
Emma M. Dangerfield
Zhimeng Wu
Mattie S.M. Timmer
Bridget L. Stocker
Chapter 7 General Preparation of Imidazole-1-sulfonate Esters
53(6)
Travis Coyle
Mark B. Richardson
Mitchell Hattie
Keith A. Stubbs
Chapter 8 Regioselective Monoacylation and Monoalkylation of Carbohydrates Catalyzed by a Diarylborinic Ester
59(8)
Doris Lee
Christopher J. Moore
Lina Chan
Mark S. Taylor
Chapter 9 The Synthesis of Carbamates from Alkenylamines
67(4)
Emma M. Dangerfield
Shivali A. Gulab
Bridget L. Stocker
Mattie S.M. Timmer
Chapter 10 Hydrolysis of Thioglycosides using Anhydrous NIS and TFA
71(6)
Ana R. de Jong
Bas Hagen
Kevin Sheerin
Jeroen D.C. Codee
Gijsbert A. van der Marel
Chapter 11 Highly Diastereoselective Construction of L-Heptosides by a Sequential Grignard Addition/Fleming-Tamao Oxidation
77(8)
Maxime Durka
Kevin Buffet
Tianlei Li
Abdellatif Tikad
Bas Hagen
Stephane P. Vincent
Chapter 12 Synthesis of Fluorinated Exo-glycals Mediated by Selectfluor
85(12)
Guillaume Eppe
Audrey Caravano
Jerome Desire
Stephane P. Vincent
Chapter 13 A Direct and Stereospecific Approach to the Synthesis of α-Glycosyl Thiols
97(10)
Roger A. Ashmus
Lei Zhang
Xiangming Zhu
Chapter 14 Efficient Microwave-Assisted Synthesis of 1',2,3,3',4,4'6-Hepta-O-benzyl-sucrose and 1',2,3,3',4,4'-Hexa-O-benzylsucrose
107(24)
M. Teresa Barros
Krasimira T. Petrova
Paula Correia-da-Silva
Ana-Paula Esteves
Section II Synthetic Intermediates
Chapter 15 Oligosaccharide-Salicylaldehyde Derivatives as Precursors of Water-Soluble, Biocompatible Anion Receptors
131(18)
Emiliano Bedini
Gianpiero Forte
Ivone Carvalho
Michelangelo Parrilli
Antonella Dalla Cort
Chapter 16 Allyl 3,4,6-Tri-O-Benzyl-α-D-Mannopyranoside
149(6)
Chakree Wattanasiri
Somsak Ruchirawat
Melanie Platon
Siwarutt Boonyarattanakalin
Chapter 17 Synthesis of a Spacer-Armed 6'-Sialyl-N-Acetyllactosamine
155(6)
G.V. Pazynina
A.A. Chinarev
A.B. Tuzikov
V.V. Nasonov
N.N. Malysheva
N.V. Bovin
Chapter 18 Synthesis of β-(1→3)-mannobiose
161(14)
Sebastien Picard
Mikael Thomas
Anne Geert Volbeda
Xavier Guinchard
David Crich
Chapter 19 Phenyl 4,6-O-Benzylidene-1-thio-α-D-mannopyranoside
175(8)
Min Huang
Huu-Anh Tran
Luis Bohe
David Crich
Chapter 20 Synthesis of 1,3,4,6-Tetra-O-acetyl-α-D-glucopyranose Revisited
183(6)
Swati S. Nigudkar
Scott J. Hasty
Monica Varese
Papapida Pornsuriyasak
Alexei V. Demchenko
Chapter 21 Synthesis of 4,6-O-Benzylidene Acetals of Methyl α-D-Glucopyranoside, Ethyl 1-Thio-β-D-gluco- and Galactopyranoside
189(8)
Papapida Pornsuriyasak
Jagodige P. Yasomanee
Edward I. Balmond
Cristina De Meo
Alexei V. Demchenko
Chapter 22 Synthesis of α-N-Acetylneuraminic Acid Methyl Glycoside
197(10)
Leonid O. Kononov
Alexander A. Chinarev
Alexander I. Zinin
Chase Gobble
Chapter 23 Synthesis of Ammonium 3-Deoxy-D-manno-oct-2-ulopyranosylonate (Ammonium Kdo)
207(6)
Hannes Mikula
Markus Blaukopf
Georg Sixta
Christian Stanetty
Paul Kosma
Chapter 24 Synthesis and Characterization of Tetra-O-propargyl Pentaerythritol
213(4)
Peng Xu
Riccardo Castelli
Pavol Kovac
Chapter 25 Improved Synthesis of Ethyl (2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1→3)-4,6-O-benzylidene-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside
217(6)
Sameh E. Soliman
Zoeisha Chinoy
Pavol Kovac
Chapter 26 Synthesis of α-D-Galactofuranosyl Phosphate
223(8)
Carla Marino
Cecilia Attorresi
Silvia Miranda
Rosa M. de Lederkremer
Chapter 27 Synthesis of 1,2:4,5-Di-O-(3,3-pentylidene)arabitol via Kinetic Acetal Formation
231(8)
Konrad Hohlfeld
Solen Josse
Sylvain Picon
Bruno Linclau
Chapter 28 1,2-Anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose
239(6)
Shino Manabe
Qingju Zhang
Yukishige Ito
Chapter 29 Synthesis of Glucosyl C-1 Dihalides from Tetra-O-acetyl-β-D-glucopyranosyl Chloride
245(8)
Jean-Pierre Praly
Tze Chieh Shiao
Chapter 30 Synthesis of 3,4,6-Tri-O-acetyl-D-galactal
253(4)
Tze Chieh Shiao
Jacques Rodrigue
Olivier Renaudet
Rene Roy
Chapter 31 Efficient Synthesis of Hepta-O-acetyl-β-lactosyl Azide via Phase Transfer Catalysis
257(6)
Tze Chieh Shiao
Denis Giguere
Nicolas Galanos
Rene Roy
Chapter 32 Synthesis of 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Azide
263(6)
Tze Chieh Shiao
Yoann M. Chabre
Myriam Roy
Rene Roy
Chapter 33 Synthesis of Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-galactopyranoside
269(6)
Tze Chieh Shiao
Denis Giguere
Patrick Wisse
Rene Roy
Chapter 34 An Alternative, Large-Scale Synthesis of 1,2:5,6-Di-O-isopropylidene-α-D-ribo-hex-3-ulofuranose
275(8)
Pavels Ostrovskis
Jevgenija Mackevica
Viktors Kumpins
Oscar Lopez
Maris Turks
Index 283
Series Editor:Pavol Ková, Ph.D., Dr. h.c., obtained his Ph.D. in organic chemistry at the Institute of Chemistry, Slovak Academy of Sciences, Bratislava. Dr. Ková is a strong promoter of good laboratory practices and a vocal critic of the publication of experimental chemistry lacking data that allow reproducibility. He has more than 40 years of experience in carbohydrate chemistry and over 280 papers published in refereed scientific journals, several patents, and book chapters. He joined the National Institutes of Health (NIH) (Bethesda, Maryland) in 1983 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, it was originally established by the American carbohydrate chemist Claude S. Hudson. Kovás main interest is the development of conjugate vaccines for bacterial diseases from synthetic carbohydrate antigens. Volume Two Editors:

Jeroen Codée obtained his Ph.D. from Leiden University, the Netherlands, under the guidance of Jacques van Boom and Stan van Boeckel in 2004. Codée then moved to the Eidgenossische Technische Hochschule (ETH) Zurich, Switzerland, for a two-year post-doctoral stay with Peter Seeberger. He subsequently returned to Leiden University, where he is now an associate professor in bio-organic chemistry. His research focuses on glycochemistry and glycobiology, ranging from fundamental organic synthesis to vaccine/drug development and the development of glycobiology tools. He has authored or co-authored more than 70 publications and seven book chapters.

Gijs van der Marel conducted his Ph.D. studies on DNA chemistry with Jacques van Boom and received his Ph.D. degree in 1981 from Leiden University, the Netherlands. He has remained associated with this university, where he is now a full professor in synthetic organic chemistry. He has supervised more than 70 Ph.D. students and authored or co-authored over 700 papers. His research focuses on all synthetic aspects of biopolymers, including nucleic acids, peptides, and carbohydrates, and hybrids and analogues thereof.
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