1st Edition
Carbohydrate Chemistry Proven Synthetic Methods, Volume 6
Foreword
Preface
List of Contributors
Editor Bios
Series Editor Bio
Chapter One: Preparation of N-Phenyltrifluoroacetimidoyl chloride (PTFAI-Cl) for the Synthesis of N-Phenyltrifluoroacetimidate (PTFAI) Donors
Jacob M. A. van Hengst, Koen Rijpkema, Koen van de Vrande, Jenny Ha, Jeroen D. C. Codée
Chapter Two: Synthesis of α-D-Idose Pentaacetate from β-D-Glucose Pentaacetate via Paulsen Acetoxonium Rearrangement
Nitish Verma, Maude Cloutier, David Clément, Charles Gauthier
Chapter Three: Synthesis of Methyl 2-deoxy-2-fluoro-α-D-mannofuranoside
Sam Bahadori, Lisa Lamine, Jessica Alcée, Surabhi Gupta, Denis Giguère
Chapter Four: Phenyl 2-azido-2,3,6-trideoxy-3,6-difluoro-1-thio-α- and β-D-glucopyranoside
Martin Kurfiřt, Fabricio Ramírez Cortés, Lucie Červenková Šťastná, Jindřich Karban
Chapter Five: Three-step Synthesis of Protected 1,6‑Di‑O‑acetyl‑D‑galactofuranoses
Michal Kratochvíl, Alexandre Grosse, Kamil Parkan
Chapter Six: Synthesis of Acyl β-C-glucosidic Compounds via Corey-Seebach Reaction
G. Jacob Boehlich, Jessica de Vries, Pieter de Saint Aulaire, Nina Schützenmeister
Chapter Seven: Synthesis of Ethyl α-Thioglycosides by Ethylation of α-Glycosyl Thiols
Zoe Beato, Markus Blaukopf, Cian Mc Carthy, Raymond Smith, Xiangming Zhu
Chapter Eight: β-L-Rhamnosylation of p-Tolyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside
Fabricio Ramírez Cortés, Aleš Krčil, Vít Novotný, Peter H. Seeberger, Petra Ménová
Chapter Nine: Optimized Synthesis of Perbenzoylated Methyl 6,6',6''-triazido-6,6',6''-trideoxy-β-maltotrioside
Dindet Steve-Evanes K.L-C Koffi Teki, Nicolas Tinet, Abed Bil, José Kovensky, Vincent Chagnault
Chapter Ten: Practical Synthesis of 2,6-Anhydro-4,5,7-tri-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
Mylène Lang, Damien Tardieu, Florian Gallier, Nicolas Kern, Philippe Compain
Chapter Eleven: 3,4,6-Tri-O-benzyl-D-Glucal and 3,4,6-Tri-O-benzyl-D-Galactal
Nicholas P. Forsythe, Emma R. Mize, Gustavo A. Kashiwagi, Alexei V. Demchenko, Hannah Wootton
Chapter Twelve: Synthesis of 1,6-Anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose
Christina Leclerc, Sam Bahadori, Jacob St-Gelais, Matteo Cattin, Denis Giguère
Chapter Thirteen: Synthesis of 3-Chloropropyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
Takaaki Goto, Martin S. Thonhofer, Paul Kosma
Chapter Fourteen: p-Tolyl 2,3,5-tri-O-acetyl-1-thio-β-D-xylofuranoside
Teddy Ehianeta, Sam Bahadori, Todd L. Lowary
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
Chun-Jui Chu, Olivier Lessard, Todd L. Lowary
Chapter Sixteen: Synthesis of Allyl 2-acetamido-2-deoxy-β-D-galactopyranoside
Jack A. Porter, Sian Berry, Calum S. Haydon, Gavin J. Miller
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
Imlirenla Pongener, Daniel Hoard, Gavin J. Miller
Chapter Eighteen: Practical Synthesis of (1S)-1-Diethylphosphonomethyl-1,5-dideoxy-1,5-imino-D-xylitol: An Analogue of α-D-Glucose-1-phosphate
Agata M. Goldmann, Jamal El-Abid, Liliane Mimoun, Floriane Heis, Isabelle Gillaizeau, Olivier R. Martin, Cyril Nicolas
Chapter Nineteen: An Easy Synthesis of C-Glucosyl Chalcones and Dihydrochalcones
Ana M. de Matos, M. Teresa Blázquez-Sánchez, Patrícia Calado, Amélia P. Rauter, Nicolas Auberger
Chapter Twenty: Synthesis of Prop-2-ynyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-β-D-glucopyranoside
Shuay Abdullayev, Samaneh Zarei, and René Roy
Chapter Twenty-One: Synthesis of 3,4-Di[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)oxy] benzaldehyde
Mohamed Touaibia, Mathilde Grosset-Magagne
Chapter Twenty-Two: Synthesis of Benzyl Protected NHPI Ester of Methyl D-Glucuronic Acid
Jenny Ha, Tom Nazé, Stéphane P. Vincent
Chapter Twenty-Three: Synthesis of 6-Bromo-6-deoxy-D-fructofuranose
Kevin M. Dorst, Hani Mobarak, Rym Yahia Boudhar, Göran Widmalm
Chapter Twenty-Four: Preparation of Gold Nanoparticles Decorated with Thiolated Galactosides
Francesca Buco, Francesca Milano, Laura Polito, Barbara Richichi, Marco Marradi
Chapter Twenty Five: 4-Bromophenyl 2,3,4-tri-O-acetyl-α-L-fucopyranoside
Rohit Chavan, Jan Veselý, Vít Novotný, Petra Ménová
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
Jacopo Tricomi, Clara De La Tramblais, Marco Marradi, Barbara Richichi
Subject Index
Cumulative Author Index Vol 1-6
Biography
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.
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 Wong
Scripps Family Chair Professor of Chemistry
The Scripps Research Institute, La Jolla, California
