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.
Synthetic Methods: Acetolysis of 6-Deoxysugars Controlled by
ArmedDisarmed Effect. NaH/Im2SO2-Mediated Preparation of Hex-2- and
Hex-3-Enopyranoside Enol Ethers. Enhancement of the Rate of Purdie
Methylation by Me2S Catalysis. Synthesis of Oligosaccharides by
Preactivation-Based Chemoselective Glycosylation of Thioglycosyl Donors. The
Use of Hypophosphorous Acid in Radical Chain Deoxygenation of Carbohydrates.
Diphenylsulfoxide-Trifluoromethanesulfonic Anhydride: A Potent Activator for
Thioglycosides. Preparation of Glycosyl Chlorides from
Glycopyranoses/Glycofuranoses under Mild Conditions. C-Glycosylation Starting
from Unprotected O-Glycosides. Palladium-Catalyzed Sonogashira Coupling on
p-Lodophenyl -d-Mannopyranoside. Synthesis by "Click Chemistry" of an
-d-Mannopyranoside Having a 1,4-Disubstituted Triazole as Aglycone.
Synthesis of Methyl Glycuronates by Chemo- and Regioselective
TEMPO/BAIB-Oxidation. Synthesis of Sugar Nucleotides: A Phosphoramidite
Approach. Conversion of N-2,2,2-Trichloroethoxycarbonyl-Protected
2-Aminoglycosides into N-Alkylated 2,3-N,O-Carbonyl Glycosides. TIBAL-Induced
Rearrangement: Synthesis of gem-Difluorocarbagalactose. Pyranose-Fused
Butenolides: An Expedient Preparation from Furanose Synthons. Glycal
Dimerization with High Diastereoselectivity. Regioselective Debenzylation of
C-Glycosylpropene. Synthesis of Azido-Functionalized Carbohydrates for the
Design of Glycoconjugates. Synthesis of Thioglycosides and Thioimidates from
Glycosyl Halides. Synthesis of Thioglycosides and Thioimidates from
Peracetates.
Synthetic Intermediates:
2-Acetamido-4,6-O-Benzylidene-2-Deoxy-d-Glucopyranose. Synthesis of
1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-,-d-Glucopyranose and
2-Azido-4,6-O-Benzylidene-2-Deoxy-,-d-Glucopyranose. An Easy Access to
2,3,4,6-Tetra-O-Benzyl-d-Galactopyranose and
2,3,6-Tri-O-Benzyl-d-Glucopyranose. Benzyl
2,3,6,2,3,6-Hexa-O-Benzyl--Cellobioside. One-Step Syntheses of
1,2,3,5,6-Penta-O-Benzoyl-,-d-Galactofuranose and
1,2,3,5-Tetra-O-Benzoyl-,-d-Arabinofuranose. Stereoselective Synthesis of
-C-Sialyl Compounds. Synthesis of O-Acetylated N-Acetylneuraminic Acid
Glycal. Substituted Benzyl Glycosides of N-Acetylneuraminic Acid. Synthesis
of 1,5-Di-C-Alkyl 1,5-Iminoxylitols Related to 1-Deoxynojirimycin. Synthesis
of 1,6-Anhydro-2,3,5-Tri-O-Benzoyl--d-Galactofuranose. Synthesis of
Prop-2-Ynyl 2,3,4,6-Tetra-O-Acetyl--d-Mannopyranoside. Synthesis of
3-C-(2,3,4,6-Tetra-O-Acetyl--d-Galactopyranosyl)prop-1-Ene. Synthesis of
(E)-Methyl 4-(2,3,4,6-Tetra-O-Acetyl--d-Galactopyranosyl)but-2-Enoate by
Cross-Metathesis Reaction. Preparation of
O--d-Galactopyranosylhydroxylamine. 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. Efficient
Synthesis of Methyl(Allyl
4-O-Acyl-2,3-Di-O-Benzyl--d-Galactopyranosid)uronates from d-Galacturonic
Acid. Methyl(Ethyl 2,3,5-Tri-O-Benzoyl-1-Thio-,-d-Galactofuranosid)uronate.
p-Tolyl 2,3,5-Tri-O-Benzoyl-1-Thio--d-Arabinofuranoside: A Useful
Thioglycoside Building Block in the Synthesis of Oligoarabinofuranosides.
Ethylene Dithioacetals of Common Hexoses. Preparation of 2,6-Anhydro-Aldose
Tosylhydrazones. Preparation of Exo-Glycals from (C-Glycopyranosyl)
formaldehyde Tosylhydrazone. Synthesis of O-(6-Deoxy-- and
-l-Galactopyranosyl) Hydroxylamines (- and
-l-Fucopyranosylhydroxylamines). Functionalization of Terminal Positions of
SucrosePart I: Synthesis of 2,3,3,4,4-Penta-OBenzylsucrose and
Differentiation of the Terminal Positions (1,6,6). Functionalization of
Terminal Positions of SucrosePart 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.
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.
