Synthesis and use of glycosyl phosphates as glycosyl donors

被引：132

作者：

Plante, OJ ^{[1
]}

Andrade, RB ^{[1
]}

Seeberger, PH ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol9905452

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Differentially protected glycosyl phosphates prepared by a straightforward synthesis from glycal precursors are used as powerful glycosyl donors. Activation of beta-glycosyl phosphates by TMSOTf at -78 degrees C achieves the selective formation of beta-glycosidic linkages in excellent yields with complete stereoselectivity. Reaction with thiois results in the conversion of glycosyl phosphates into thioglycosides in nearly quantitative yield. An orthogonal coupling strategy using glycosyl phosphate donors and thioethyl glycoside accepters allows for the rapid synthesis of a trisaccharide.

引用

页码：211 / 214

页数：4

共 27 条

[1] TOTAL SYNTHESIS OF BLEOMYCIN A(2) AND RELATED AGENTS .4. SYNTHESIS OF THE DISACCHARIDE SUBUNIT - 2-O-(3-O-CARBAMOYL-ALPHA-D-MANNOPYRANOSYL)-L-GULOPYRANOSE AND COMPLETION OF THE TOTAL SYNTHESIS OF BLEOMYCIN A(2) [J].