Kosma P., Wrodnigg T., Stütz A. (eds.) Carbohydrate Chemistry: Proven Synthetic Methods, Volume 5

CRC Press, 2021. — 345 p. — ISBN 978-0-367-56173-4.This fully updated and expanded second edition of a highly popular text book focuses on the structure and mechanism in carbohydrate chemistry and biochemistry.
Carbohydrates play important roles in biological systems as energy sources, as structural materials, and as informational structures (when they are often attached to proteins or lipids). Their chemical reactivity and conformational behaviour is governed by mechanistic and stereochemical rules, which apply as much to enzymic as to non-enzymic reactivity. The same principles of reactivity and conformation govern changes brought about in the process industries, such as pulp, paper and food.
Extensively referenced with citations and a detailed index, the book contains everything the reader needs to know to start a carbohydrate research project with one of the real strengths being the treatment and integration of the important physical-chemical principles and methods (though lead references only are given to the finer points of carbohydrate synthesis).
The book is suitable for both researchers who are new to the subject and those more established as well as a readership from diverse backgrounds and interests, including chemists, biochemists, food scientists and technologists involved with the processing of polysaccharides in the paper, textile, cosmetics, biofuels and other industries.Synthetic Methods
Synthesis of Glycosyl Thiols via 1,4-Dithiothreitol-Mediated Selective Anomeric S-Deacetylation
One-Step Transformation of Glycals into 1-Iodo Glycals
Optimized Henry Reaction Conditions for the Synthesis of an l-Fucose C-Glycosyl Derivative
Microwave-Assisted Synthesis of N-Substituted 1-Azido Glucuronamides
Click Approach to Lipoic Acid Glycoconjugates
Synthesis of N-Glucosyl Ethyl and Butyl Phosphoramidates
p-Tolyl 2,3,4,6-Tetra-O-Benzoyl-1-Thio-β-d-Galactopyranoside: Direct Synthesis from the Readily Available α-per-O-Benzoyl Derivative
One-Pot Chemoselective S- vs O-Deacetylation and Subsequent Thioetherification
Sakurai Anomeric Allylation of Methyl α-Pyranosides
Conversion of Simple Sugars to Highly Functionalized Fluorocyclopentanes
Carbene-Mediated Quaternarization of the Anomeric Position of Carbohydrates
Synthetic Intermediates
Glucose and Glucuronate 2,2,2-Trichloroethyl Sulfates: Precursors for Multiply Sulfated Oligosaccharides
Synthesis of Allyl α-(1→2)-Linked α-Mannobioside from a Common 1,2-Orthoacetate Precursor
Synthesis of 2I-O-Propargylcyclo-Maltoheptaose and Its Peracetylated and Hepta(6-O-Silylated) Derivatives
Synthesis of 1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy-α,β-d-Galactopyranose
Regioselective Palladium Catalyzed Oxidation at C-3 of Methyl Glucoside
Synthesis of Dibenzyl 2,3,4,6-Tetra-O-Benzyl-α-DMannopyranosyl Phosphate
Synthesis and Characterization of (+)-3-C-Nitromethyl-1,2:5,6-di-O-Isopropylidene-α-d-Allofuranose
Synthesis and Characterization of Propargyl 2,3,4,6-Tetra-OAcetyl-β-d-Glucopyranoside
3-(2′,3′,4′-Tri-O-Acetyl-α-l-Fucopyranosyl)-1-Propene
Synthesis and Characterization of 4-Methylphenyl 2,3,4,6-Tetra-O-Benzoyl-1-Thio-β-d-Galactopyranoside
Alternative Synthesis of 1,2,4,6-Tetra-O-Acetyl-3-Deoxy-3-Fluoro-α,β-d-Glucopyranose
Synthesis of Methyl 4-O-Benzoyl-2,3-O-Isopropylidene-α-d-Rhamnopyranoside: A Precursor to d-Perosamine
Synthesis of Allyl and Dec-9-Enyl α-d-Mannopyranosides from d-Mannose
Synthesis of 2,2,2-Trifluoroethyl Glucopyranoside and Mannopyranoside via Classical Fischer Glycosylation
Synthesis of 2-{2-[2-(N-Tert-Butyloxycarbonyl)Ethoxy]Ethoxy} Ethyl β-d-Glucopyranoside
Synthesis of 2-Propynyl 2-Acetamido-3,4,6-Tri-O-Acetyl-2-Deoxy-1-Thio-β-d-Glucopyranoside, 2-Propynyl 3,4,6-Tri-OAcetyl-2-Deoxy-2-Phthalimido-1-Thio-β-d-Glucopyranoside and Their 2-(2-Propynyloxy-ethoxy)ethyl Analogs
Synthesis of 1′-(4′-Thio-β-d-Ribofuranosyl) Uracil
Synthesis of an Orthogonally Protected l-Idose Derivative Using Hydroboration/Oxidation
4-O-Acetyl-2-Azido-3,6-di-O-Benzyl-2-Deoxy-α/β-d-Glucopyranose
2,3,4-Tri-O-Benzoyl-6-O-(Tert-Butyldiphenylsilyl)-1-Thio-β-d-Glucopyranose
Phenyl 2-Azido-4,6-di-O-Benzyl-2,3-Dideoxy-3-Fluoro-1-Thio-α- and β-d-Glucopyranosides
An Alternative Synthesis of 3-Azidopropyl 2,4,6-Tri-OBenzyl-β-d-Galactopyranosyl-(1→4)-2,3,6-Tri-O-Benzyl-β-d-Glucopyranoside