α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose |
| |
| Institution: | 1. Institute of Physics, Faculty of Physics, Astronomy and Informatics, Nicolaus Copernicus University, Grudzi?dzka 5/7, Toruń, Poland;2. Department of Electronics and Computer Science, Koszalin University of Technology, 2 ?niadeckich St., Koszalin 75-453, Poland;3. State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Rd 38, Beijing 100191, China;;4. National Glycoengineering Research Center, and State Key Laboratory of Microbial Technology, Shandong University, Jinan 250100, China;1. Department of Oral and Maxillofacial Surgery, Hannover Medical School, Germany;2. Department of Small Cloven-Hoofed Animals, University of Veterinary Medicine Hannover, Germany;3. Department of Small Animals, University of Veterinary Medicine Hannover, Germany;4. Department of Traumatology and Regenerative Joint Surgery, Hannover Medical School, Germany |
| |
| Abstract: | The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an α-glycoside was desired. Although most acceptor–donor pairs led to predominantly or exclusively the β-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of α,β arylglycosides. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
