Effective protection of the N-sulfate of glucosamine derivatives with the 2,2,2-trichloroethyl group

被引：16
|
作者：
Chen, Jianfang [1 ]
Yu, Biao [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 10期
基金：
中国国家自然科学基金;
关键词：
2,2,2-trichloroethyl (TCE) group; N-sulfate; glucosamine; protecting group; glycosylation;
D O I：
10.1016/j.tetlet.2007.12.132
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 2,2,2-trichloroethyl (TCE) group was utilized as the first protecting group for N-sulfates (chlorosulfuric acid TCE ester, Et3N, DMAP, DMF). Glycosylation with 3,4,6-tri-O-acetyl-N-trichloroethylsulfuryl-alpha-D-glucosaminosyl trichloroacetimidate provided the corresponding beta-glucosaminosides stereoselectively and in excellent yields. The TCE protection stayed stable under a variety of conditions for the manipulation of other protecting groups, and was readily removable with zinc in the presence of ammonium chloride in methanol. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1682 / 1685
页数：4
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