Stereodirecting Effects of 4-O-ortho-cyanobenzyl Ether on Chemical Glycosylation with Glucopyranosyl Donor  

作　　者：Han Zhang Aoxin Guo Youhui Meng Yue Wang Jian Gao Xue-Wei Liu 

机构地区：[1]National Glycoengineering Research Center Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology,NMPA Key Laboratory for Quality Research and Evaluation of Carbohydrate-based Medicine,Shandong University,Qingdao,Shandong 266237,China [2]Division of Chemistry and Biological Chemistry,School of Physical and Mathematical Sciences,Nanyang Technological University 21NanyangLink,Singapore 637371,Singapore

出　　处：《Chinese Journal of Chemistry》2023年第6期651-656,共6页中国化学（英文版）

基　　金：This work was supported by the National Natural Science Foundation of China(22177060);the Young Scholars Program of Shandong University(2018WLJH41);the Central Government Guide Local Science and Technology Development Funds(No.YDZX20203700002579).

摘　　要：Here we report a systematic investigation on the stereodirecting effects of a 4-O-ortho-cyanobenzyl ether(oBCN)group with a glucopyranosyi donor.Experimental studies revealed that the glycosylation reactions using this donor generally show dual-stereoselectivities depending on the acceptor nucleophilicity,that is,glycosylation of weak nucleophile acceptors generally affordsα-glycosides specifically while glycosylation of strong nucleophile acceptors affords β-glycosides preferentially.

关 键 词：GLYCOSYLATION OLIGOSACCHARIDES DIASTEREOSELECTIVITY Cyanobenzyl ether Hydrogen bonds 

分 类 号：O62[理学—有机化学]