Carbohydrate Chemistry

Christian Vogel earned a PhD in organic chemistry–heterocyclic chemistry under the supervision of Professor Klaus Peseke at the University of Rostock in 1980. Since 1992, he has served as a professor in the Department of Organic Chemistry, University of Rostock. In addition to fucose chemistry, Dr. Vogel’s main interests are pectin fragment synthesis using the modular design principle, the synthesis of rare sugars for structural investigations, and C-nucleosides.  Paul V. Murphy was appointed to the position of Established Professor of Chemistry at National University of Ireland Galway (NUI Galway) in 2008. He is from the West of Ireland (Turloughmore, Co. Galway). His group is engaged in the design and synthesis of bioactive compounds, with a focus on carbohydrates, maintaining a long tradition in carbohydrate research in Galway’s School of Chemistry.

Foreword

Introduction

Editors

Series Editor

Contributors

Section I Synthetic Methods

Chapter 1 Picoloyl-Protecting Group in Oligosaccharide Synthesis: Installation, H-Bond-Mediated Aglycone Delivery (HAD), and Selective Removal

Michael P. Mannino, Jagodige P. Yasomanee, Alexei V. Demchenko, and Venukumar Patteti

Chapter 2 Monomethoxytrityl (MMTr) as an Efficient S-Protecting Group in the Manipulation of Glycosyl Thiols

Raymond Smith, Xiangming Zhu, and Elena Calatrava-Pérez

Chapter 3 One-Step Inversion of Configuration of a Hydroxy Group in Carbohydrates

Shino Manabe and Markus Blaukopf

Chapter 4 Formation and Cleavage of Benzylidene Acetals Catalyzed by NaHSO4∙SiO2

Lifeng Sun, Xin-Shan Ye, and Xingdi Wang

Chapter 5 Thiodisaccharides by Photoinduced Hydrothiolation of 2-Acetoxy Glycals

Dániel Eszenyi, László Lázár, Anikó Borbás, and

Ruairi O. McCourt

Chapter 6 One-Step Preparation of Protected N-tert-Butanesulfinyl d-ribo and d-xylo Furanosylamines from Related Sugar Hemiacetals

Chloé Cocaud, Cyril Nicolas, Olivier R. Martin, and Jérôme Désiré

Chapter 7 An Alternative Preparation of Azides from Amines via Diazotransfer with Triflyl Azide

Yuqian Ye, Xin-Shan Ye, and Xingdi Wang

Chapter 8 Simple Preparation of Dimethyldioxirane and Its Use as an Epoxidation Agent for the Transformation of Glycals to Glycosyl Phosphates

Katharina Kettelhoit, Daniel B. Werz, Aniruddha Sasmal, Xinyu Liu, and Philipp Gritsch

Chapter 9 Preparation of Glycosyl Bromides of α-d-Gluco-hept-2-ulopyranosonic Acid Derivatives

Veronika Nagy, Katalin Czifrák, László Juhász, László Somsák, and Olena Apelt

Chapter 10 Preparation of 2,6-Anhydro-hept-2-enonic Acid Derivatives and Their 3-Deoxy Counterparts

Sándor Kun, Szabina Deák, Katalin Czifrák, László Juhász, László Somsák, and Olena Apelt

Section II Synthetic Intermediates

Chapter 11 Synthesis of 4-Nitrophenyl β-d-galactofuranoside: A Useful Substrate for β-d-Galactofuranosidases Studies

Carla Marino, Santiago Poklepovich Caridea, Rosa M. de Lederkremer, and Sydney Villaume

Chapter 12 Synthesis of Benzoylated β-d-Glucosamine Derivatives

Claudia Di Salvo, Karen A. Fox, Paul V. Murphy, and Jens Langhanki

Chapter 13 Synthesis of 3,4,6-Tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-α-d-glucopyranose

Vimal K. Harit, Namakkal G. Ramesh, and Srinivasa-Gopalan Sampathkumar

Chapter 14 A Convenient Synthesis of 3,4-Di-O-acetyl-d-rhamnal (3,4-Di-O-acetyl-6-deoxy-d-glucal)

Jessica N. Spradlin, Dina Lloyd, Clay S. Bennett, and Chao Liang

Chapter 15 One-Pot Synthesis of 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-d-glucopyranose Using Anomeric O-Acylation

Sergey S. Pertel, Elena S. Kakayan, Sergey A. Seryi, and Anthony W. McDonagh

Chapter 16 1,2,3,5,6-Penta-O-tert-butyl(dimethyl)silyl-β-d-galactofuranose: A Versatile Glycosylating Agent for Galactofuranosylation

Diego González-Salas, Carla Marino, and Mónica Guberman

Chapter 17 Per-O-benzoyl-1,2-O-benzylidene derivatives of Pyranoses and Furanoses—Versatile Building Blocks for Oligosaccharide Synthesis

Polina I. Abronina, Alexander I. Zinin, Nikita M. Podvalnyy, Leonid O. Kononov, and Sandip Pasari

Chapter 18 Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-α,β-dglucopyranose Using the Diazo-Transfer Reagent Imidazole-1-sulfonyl Azide Hydrogen Sulfate

Garrett T. Potter, Gordon C. Jayson, John M. Gardiner, Lorenzo Guazelli, and Gavin J. Miller

Chapter 19 Synthesis of Methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-and β-d-glucopyranosides

Alexander S. Henderson, M. Carmen Galan, and Carlo Pifferi

Chapter 20 Ring-Opening of Benzylated Gluconolactone to Access Useful Gluconamide Conjugates

Sarah Roy, Vincent Denavit, Tze Chieh Shiao, and Denis Giguère

Chapter 21 A Multigram Synthesis of Phenyl 2-azido-3-O-benzyl-4,6-Obenzylidene-2-deoxy-1-thio-α-d-mannopyranoside

Ivan A. Gagarinov, Apoorva D. Srivastava, Geert-Jan Boons, and Zhen Wang

Chapter 22 Preparation and Characterization of 6-Azidohexyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside

Divya Kushwaha, Pavol Kováč, and Marek Baráth

Chapter 23 Synthesis of (2S, 3S, 4S)-2,3,4-Tri-O-benzyl-5-bromopentanenitrile

Michał Malik, Sławomir Jarosz, and Anna Zawisza

Chapter 24 Simplifying Access to 3,4-Di-O-acetyl-1,5 anhydro-2,6-dideoxy-d-lyxo-hex-1-enitol (3,4-Di-O-acetyl-d-fucal)

Ivan A. Gagarinov, Apoorva D. Srivastava, Geert-Jan Boons, and Satsawat Visansirikul

Chapter 25 2-Chloroethyl and 2-Azidoethyl 2,3,4,6-tetra-O-acetyl-β-dgluco-and β-d-galactopyranosides

Andrew Reddy, Jessica Ramos-Ondono, Lorna Abbey, Trinidad Velasco-Torrijos, and Thomas Ziegler

Chapter 26 Synthesis of Heptakis(6-O-tert-butyldimethylsilyl) cyclomaltoheptaose

Juan M. Casas-Solvas, Antonio Vargas-Berenguel, and Milo Malanga

Chapter 27 Sodium d-galactonate, d-Galactono-1,4-lactone, and Synthetically Useful Methyl d-galactonates

Verónica Rivas, Adriana A. Kolender, Oscar Varela, and Gilbert Duhirwe

Chapter 28 Synthesis of a 3,6-Orthogonally-Protected Mannopyranoside Building Block

Sarah Roy, Vincent Denavit, Danny Lainé, Denis Giguère, and Julia Meyer

Chapter 29 Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(bis-methoxycarbonyl) methyl]-β-d-glucopyranoside

Prashant Pavashe, Tukaram Pimpalpalle, Torsten Linker, and László Juhász

Chapter 30 Fluorine-Containing Carbohydrates: Synthesis of 6-Deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene-α-d-galactopyranose

Vincent Denavit, Danny Lainé, Denis Giguère, and Guillaume Le Heiget

Chapter 31 A Facile Synthesis of 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-trifluoroacetamido-β-d-glucopyranose

Nikita M. Podvalnyy, Yakov V. Voznyi, Alexander I. Zinin, Polina I. Abronina, Leonid O. Kononov, and Salvatore G. Pistorio

Chapter 32 An Expeditious Route to an HO-4 Free d-GalNAc Building Block from d-GlcNAc

Francisco Santoyo-Gonzalez, Fernando Hernandez-Mateo, F. J. Lopez-Jaramillo, and Clara Uriel

Chapter 33 Improved Synthesis of 3-(2-Deoxy-β-d-erythro-pentofuranos-1-yl) prop-1-ene

Heike Wächtler, Dilver Peña Fuentes, Olena Apelt, Christian Vogel, Dirk Michalik, and Mykhaylo A. Potopnyk

Chapter 34 Improved Synthesis of 3-(β-d-Ribofuranos-1-yl) prop-1-ene

Heike Wächtler, Dilver Peña Fuentes, Olena Apelt, Christian Vogel, Dirk Michalik, and Mykhaylo A. Potopnyk

Chapter 35 3-Azidopropyl 2-Acetamido-2-deoxy-α-d-glucopyranoside

Jean-Baptiste Farcet, Anna Christler, Paul Kosma, and Mihály Herczeg

Chapter 36 Large-Scale Synthesis of 2,3,4,6-Tetra-O-benzyl-1-deoxynojirimycin

Damien Hazelard, Mathieu L. Lepage, Jérémy P. Schneider, Maëva M. Pichon, Philippe Compain, and Fabien Massicot

Chapter 37 Synthesis of Indol-3-yl Glucuronides for Monitoring Glucuronidase Activity

Stephan Böttcher, Christian Czaschke, Joachim Thiem, and Mauro Pascolutti

Chapter 38 Preparation of 2,6-Anhydro-3,4,5,7-tetra-O-benzyl-d-glycero-dgulo-heptonimidamide

Eszter Szennyes, Éva Bokor, Attila Kiss, László Somsák, and Yoann Pascal

Chapter 39 Allyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-dglucopyranoside

Yann Le Guen, Pierre Chassagne, Guillaume Le Heiget, Dominique Urban, and Laurence A. Mulard

Chapter 40 1,2-Bis (diphenylphosphano) Ethane (DPPE)-Mediated Synthesis of Glycosyl Amides

David P. Temelkoff, Peter Norris, and Adele Gabba

Index