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 Count