正交保护壳寡糖的制备：异常远程取代基效应的观察

Preparation of orthogonally protected chitosan oligosaccharides: observation of an anomalous remote substituent effect.

作者信息

Liew Siong-Tern, Wei Alexander

机构信息

Department of Chemistry, Purdue University, West Lafayette, IN 47907-1393, USA.

出版信息

Carbohydr Res. 2002 Aug 16;337(14):1319-24. doi: 10.1016/s0008-6215(02)00124-6.

DOI:10.1016/s0008-6215(02)00124-6

PMID:12151213

Abstract

Orthogonally protected chitosan tetrasaccharides were synthesized in a convergent fashion by trichloroacetimidate activation. The anomeric substituent at the reducing end of the disaccharide acceptor has a remarkably strong influence on glycosidic coupling; a thiophenyl-substituted disaccharide was observed to be an unusually poor glycosyl acceptor in comparison with the corresponding allyloxy-substituted disaccharide.

摘要

通过三氯乙酰亚胺酯活化以汇聚方式合成了正交保护的壳四糖。二糖受体还原端的异头取代基对糖苷偶联有显著的强烈影响；与相应的烯丙氧基取代的二糖相比，观察到硫代苯基取代的二糖是一种异常差的糖基受体。