A novel method for stereoselective glycosidation with thioglycosides: Promotion by hypervalent iodine reagents prepared from PhIO and various acids.

被引：63

作者：

Fukase, K

Kinoshita, I

Kanoh, T

Nakai, Y

Hasuoka, A

Kusumoto, S

机构：

[1] Department of Chemistry, Faculty of Science, Osaka University, Toyonaka

来源：

TETRAHEDRON | 1996年 / 52卷 / 11期

关键词：

D O I：

10.1016/S0040-4020(96)00057-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Combinations of iodosobenzene (PhIO) and various acids effectively promote glycosidation using thioglycosides as glycosyl donors. beta-Selective glucosidation was effected by use of TfOH, Tf(2)O, TMSOTf, Sn(OTf)(2), and Yb(OTf)(3) as catalysts with 2-O-benzoylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the solvent effect of acetonitrile, respectively. Combinations of PhIO with SnCl2-AgClO4, SnCl4-AgClO4, BiCl3-AgClO4, and SbCl3-AgClO4 in ether were advantageous for alpha-glucosidation, where 2,2,2-trichloroethoxycarbonyl group introduced at the 6-position of a 2-O-benzylated donor remarkably increased alpha-selectivity.

引用

页码：3897 / 3904

页数：8

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[21] A MILD AND GENERAL-METHOD FOR THE SYNTHESIS OF O-GLYCOSIDES [J].