Carbohydrate Chemistry

Denis Giguère obtained his undergraduate degree in Biopharmaceutical Sciences from the University of Ottawa (Canada) in 2003. He earned his M.Sc. in organic chemistry with René Roy at Université du Québec à Montréal (Canada) and his Ph.D. with Stephen Hanessian at Université de Montréal (Canada) working on the synthesis of 4-deoxyhexopyranoses, C-disaccharides, and biologically active C-glycosides. He trained as a postdoctoral fellow with K. C. Nicolaou at the Scripps Research Institute (USA) working on the total synthesis of dithiodiketopiperazine natural products. After two years working in industry, he started his independent career at Université Laval (Canada) as an Assistant professor of Chemistry in 2014 and in 2019 was promoted to Associate professor. He is a Full professor since 2023 and was invited professor at Université de Caen in 2024. His research group focuses on the preparation of halogenated carbohydrates, glycomimetics, and complex saccharides, as well as the development of synthetic methodologies related to carbohydrate synthesis.Stéphane Vincent received his Master and PhD degrees in bioorganic chemistry from the Université Louis Pasteur (Strasbourg, France) with Charles Mioskowski. After postdoctoral studies first at The Scripps Research Institute in the research group of Prof. Chi-Huey Wong and then in Strasbourg with Prof. Jean-Marie Lehn, he took up a permanent position as a CNRS researcher in 2001 at the Ecole Normale Supérieure (Paris). In 2004, he began an appointment at Université de Namur (Belgium), as Assistant Professor then Full Professor in 2014. His research interests include glycosciences, biocatalysis, and the chemistry of infectious diseases.

• Foreword. Preface. Guidelines for Authors. Remarks by the Series Editor. List of Contributors. About the Editors. About the Series Editor. Introduction. Chapter One: Preparation of N-Phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) for the Synthesis of N-Phenyltrifluoroacetimidate (PTFAI) Donors. Chapter Two: Synthesis of α-D-Idose Pentaacetate from β-D-Glucose Pentaacetate via Paulsen Acetoxonium Rearrangement. Chapter Three: Synthesis of Methyl 2-deoxy-2-fluoro-α-D-mannofuranoside. Chapter Four: Phenyl 2-azido-2,3,6-trideoxy-3,6-difluoro-1-thio-α- and β-D-glucopyranoside. Chapter Five: Three-step Synthesis of Protected 1,6‑Di‑O‑acetyl‑D‑galactofuranoses. Chapter Six: Synthesis of Acyl β-C-glucosidic Compounds via Corey-Seebach Reaction. Chapter Seven: Synthesis of Ethyl α-Thioglycosides by Ethylation of α-Glycosyl Thiols. Chapter Eight: β-L-Rhamnosylation of p-Tolyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside. Chapter Nine: Optimized Synthesis of Perbenzoylated Methyl 6,6',6''-triazido-6,6',6''-trideoxy-β-maltotrioside. Chapter Ten: Practical Synthesis of 2,6-Anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-hept-1-enitol. Chapter Eleven: 3,4,6-Tri-O-benzyl-D-Glucal and 3,4,6-Tri-O-benzyl-D-Galactal. Chapter Twelve: Synthesis of 1,6-Anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose. Chapter Thirteen: Synthesis of 3-Chloropropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside. Chapter Fourteen: p-Tolyl 2,3,5-tri-O-acetyl-1-thio-β-D-xylofuranoside. Chapter Fifteen: 4,6-O-Benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-β-D-glucopyranosyl Fluoride: A Crystalline and Versatile Building Block for Oligosaccharide Synthesis. Chapter Sixteen: Synthesis of Allyl 2-acetamido-2-deoxy-β-D-galactopyranoside. Chapter Seventeen: Synthesis of Orthogonally Protected p-Tolyl 2-azido-3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-levulinoyl-1-thio-β-D-glucopyranoside. Chapter Eighteen: Practical Synthesis of (1S)-1-Diethylphosphonomethyl-1,5-dideoxy-1,5-imino-D-xylitol: An Analogue of α-D-Glucose-1-phosphate. Chapter Nineteen: An Easy Synthesis of C-Glucosyl Chalcones and Dihydrochalcones. Chapter Twenty: Synthesis of Prop-2-ynyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranoside. Chapter Twenty-One: Synthesis of 3,4-Di[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy] benzaldehyde. Chapter Twenty-Two: Synthesis of Benzyl Protected NHPI Ester of Methyl D-Glucuronic Acid. Chapter Twenty-Three: Synthesis of 6-Bromo-6-deoxy-D-fructofuranose. Chapter Twenty-Four: Preparation of Gold Nanoparticles Decorated with Thiolated Galactosides. Chapter Twenty Five: 4-Bromophenyl 2,3,4-tri-O-acetyl-α-L-fucopyranoside. Chapter Twenty Six: Synthesis of Methyl 2-(4-[2,3,4,6-tetra-O-acetyl-α,β-D-galactopyranosyloxy]phenyl)acetate and Methyl 2-(4-[2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy]phenyl)acetate. Subject Index. Cumulative Author Index Vol 1-6.

Carbohydrates are the most abundant organic molecules on earth and are one of the four major classes of biomolecules that make up cells. However, they exist in nature as heterogeneous mixtures or conjugates with proteins and lipids and are extremely difficult to isolate as pure and homogeneous forms for the study of their structure and function. Therefore, synthetic carbohydrate chemistry with chemical or biological means or a combination of both has been the most effective way of obtaining carbohydrates with defined structure for the study.Over the years, many chemical methods have been developed, mainly through protecting group manipulation and stereoselective glycosylation, for the synthesis of carbohydrates in various forms and significant progress has been made to improve our understanding of this class of molecules.This new volume of Carbohydrate Chemistry - Proven Synthetic Methods edited by Professors S. Vincent and D. Giguère provides detailed procedures from leading scientists for the synthesis of glycans and their intermediates as well as building blocks. A key feature in this volume is the appropriate choice of protecting and leaving groups for the building blocks and the stereoselective control of glycosylation reaction. As demonstrated in previous volumes, the standard protocol provided in each chapter of this carbohydrate chemistry series is of significant value to those who want to access various forms of carbohydrates for investigation.Chi-Huey WongScripps Family Chair Professor of ChemistryThe Scripps Research Institute, La Jolla, California