A highly reactive and stereoselective β-mannopyranosylation system:: Mannosyl 4-pentenoate/PhSeOTf

被引：65

作者：

Baek, Ju Yuel

Choi, Tae Jin

Jeon, Heung Bae

Kim, Kwan Soo ^{[1
]}

机构：

[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

[2] Yonsei Univ, Ctr Bioact Mol Hybrids, Seoul 120749, South Korea

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 44期

关键词：

beta-mannopyranosylation; glycosides; glycosyl pentenoate; glycosylation; phenylselenyl triflate;

D O I：

10.1002/anie.200602642

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Controlled linkage: PhSeOTf-promoted glycosylations of a variety of acceptor alcohols with 4,6-O-benzylidene-2,3-di- O-benzylmannopyranosyl pentenoate afford β-mannopyranosides in high yields and with excellent stereoselectivity (see scheme). This method is even better than other known methods for the mannosylation of simple reactive primary alcohols. Tf=trifluoromethanesulfonyl, TTBP = 2,4,6-tri-tert-butylpyrimidine. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：7436 / 7440

页数：5

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