Effective protection of the N-sulfate of glucosamine derivatives with the 2,2,2-trichloroethyl group
Effective protection of the N-sulfate of glucosamine derivatives with the 2,2,2-trichloroethyl group
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DOI：
10.1016/j.tetlet.2007.12.132
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发表时间：
2008-03-03
影响因子：
1.8
通讯作者：
Yu, Biao
中科院分区：
文献类型：
--
作者：
Chen, Jianfang;Yu, Biao
利用2，2，2-三氯乙基(TCE)作为N-硫酸盐(氯硫酸TCE酯，Et3N，DMAP，DMF)的第一保护基团。与3，4，6-tri-O-acetyl-N-trichloroethylsulfuryl-alpha-D-glucosaminosyl三氯乙酰亚氨酸酯的糖基化反应以立体选择性和极高的产率提供了相应的β-氨基葡萄糖苷。对于其他保护基团的操纵，TCE保护在各种条件下保持稳定，并且在甲醇中存在氯化铵的情况下，可以很容易地与锌一起移除。(C)2008爱思唯尔有限公司。保留所有权利。
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.