Use of phenyl 2-α-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions
Use of phenyl 2-α-selenoglycosides of N-acetylneuraminic acid as a glycosyl donor for the glycosylation reactions
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DOI：
10.1016/s0960-894x(02)00400-6
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发表时间：
2002-09-02
影响因子：
2.7
通讯作者：
Sato, M
中科院分区：
文献类型：
--
作者：
Ikeda, K;Sugiyama, Y;Sato, M
在N，N-二异丙基乙胺存在下，Neu 5Ac 1的全乙酰化氯代衍生物与苯硒醇反应，以高产率合成了Neu 5Ac 2的苯基2-α-硒代糖苷。在NIS/TfOH或DMTST的催化下，2与各种醇的反应都能以中等产率得到各种糖苷。还实现了用AgOTf/K2 CO 3对2的选择性活化超过Neu 5Ac 6的苯基2-α-硫代糖苷。(C)2002爱思唯尔科技有限公司版权所有。
Phenyl 2-alpha-selenoglycosides of Neu5Ac 2 were successfully prepared from the corresponding peracetylated chloro derivative of Neu5Ac 1 and phenylselenol in the presence of N,N-di-isopropylethylamine in excellent yields. The reaction of 2 with various alcohols was effectively catalyzed by NIS/TfOH or DMTST to produce a variety of glycosides in moderate yields. Selective activation of 2 over phenyl 2-alpha-thioglycoside of Neu5Ac 6 with AgOTf/K2CO3 was also achieved. (C) 2002 Elsevier Science Ltd. All rights reserved.