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Full Description
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-α-d-mannopyranoside, 1,2-anhydro-3,4,6-tri-O-benzyl-β-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.
Contents
Section I: Synthetic Methods. Highly Stereoselective 1,2-cis-Glycosylations Employing C-2 (S)-(Phenylthiomethyl)benzyl Ether as a Chiral Auxiliary. Regioselective Reductive Openings of 4,6-O-Benzylidene-Type Acetals Using LiAlH4-AlCl3. A Facile Method for Oxidation of Primary Alcohols to Carboxylic Acids in Carbohydrate Synthesis. Ultrasonic Energy Promoted Allylation to Generate 1-C-(2,3,4,6-Tetra-O-benzyl-α-d-glucopyranosyl)prop-2-ene. Synthesis of a Multivalent Glycocyclopeptide Using Oxime Ligation. Reductive Amination Methodology for Synthesis of Primary Amines from Unprotected Synthons. General Preparation of Imidazole-1-sulfonate Esters. Regioselective Monoacylation and Monoalkylation of Carbohydrates Catalyzed by a Diarylborinic Ester. The Synthesis of Carbamates from Alkenylamines. Hydrolysis of Thioglycosides Using Anhydrous N-Iodosuccinimide (NIS) and Trifluoroacetic Acid (TFA). Highly Diastereoselective Construction of l-Heptosides by a Sequential Grignard Addition/Fleming-Tamao Oxidation. Synthesis of Fluorinated Exo-glycals Mediated by Selectfluor. A Direct and Stereospecific Approach to the Synthesis of α-Glycosyl Thiols. 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. Section II: Synthetic Intermediates. Oligosaccharide-Salicylaldehyde Derivatives as Precursors of Water-Soluble, Biocompatible Anion Receptors. Allyl 3,4,6-Tri-O-Benzyl-α-d-Mannopyranoside. Synthesis of a Spacer-Armed 6'-Sialyl-N-Acetyllactosamine. Synthesis of β-(1→3)-mannobiose. Phenyl 4,6-O-Benzylidene-1-thio-α-d-mannopyranoside. Synthesis of 1,3,4,6-Tetra-O-acetyl-α-d-glucopyranose Revisited. Synthesis of 4,6-O-Benzylidene Acetals of Methyl α-d-Glucopyranoside, Ethyl 1-Thio-β-d-gluco- and Galactopyranoside. Synthesis of α-N-Acetylneuraminic Acid Methyl Glycoside. Synthesis of Ammonium 3-Deoxy-d-manno-oct-2-ulopyranosylonate (Ammonium Kdo). Synthesis and Characterization of Tetra-O-propargyl Pentaerythritol. 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. Synthesis of α-d-Galactofuranosyl Phosphate. Synthesis of 1,2 4,5-Di-O-(3,3-pentylidene)arabitol via Kinetic Acetal Formation. 1,2-Anhydro-3,4,6-tri-O-benzyl-β-d-mannopyranose. Synthesis of Glucosyl C-1 Dihalides from Tetra-O-acetyl-β-d-glucopyranosyl Chloride. Synthesis of 3,4,6-Tri-O-acetyl-d-galactal. Efficient Synthesis of Hepta-O-acetyl-β-lactosyl Azide via Phase Transfer Catalysis. Synthesis of 2,3,4,6-Tetra-O-acetyl-α-d-mannopyranosyl Azide. Synthesis of Phenyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-d-galactopyranoside. An Alternative, Large-Scale Synthesis of 1,2 5,6-Di-O-isopropylidene-α-d-ribo-hex-3-ulofuranose.
