Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem.
Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences.
Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods.
The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.
Table of Contents
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
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.
'The contributors are the best scientists in the field and the series editor is highly respected. The volumes will ... be of use to undergraduates involved in carbohydrate workshops.'
– Alexei Demchenko, Associate Professor of Chemistry and Biochemistry, Director of Graduate Studies, University of Missouri – St. Louis.
‘This essential book series, focused on carbohydrate synthesis, starts with a dedication to Nobel Laureate Sir John W. Cornforth, who is credited with the first public criticism of what he pictured as ‘pouring a large volume of unpurified sewage into the chemical literature.’1 Unfortunately, this issue is not limited to the field of chemistry as many high profile cases of irreproducible experiments have led to alarms being set off even in the popular press.2 This series then serves as the much-needed water treatment plants – places where the reader can be guaranteed a good clean reproducible experiment. … at least now chemists with or without expertise in carbohydrates can count on finding reliable procedures to make sugar-based compounds at one scale – a major achievement. Not only should current practitioners gain back time lost in attempts to properly reconstruct experimental procedures, but these procedures should also allow more creative scientists to contribute to this growing area.
- Cornforth JW. Austr. J. Chem. 1993;46:157e70.
- For example, see Unreliable research: trouble at the lab. Econ. October 19, 2013.’
– Nicola L.B. Pohl, Indiana University, Department of Chemistry, Bloomington, IN, USA, for Carbohydrate Research, http://dx.doi.org/10.1016/j.carres.2015.04.007.