Revisiting the armed-disarmed concept: The importance of anomeric configuration in the activation of S-Benzoxazolyl glycosides

被引：54

作者：

Crich, David ^{[1
]}

Li, Ming ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 21期

关键词：

D O I：

10.1021/ol701466u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.

引用

页码：4115 / 4118

页数：4

共 19 条

[1]

Anslyn E. V., 2006, MODERN PHYS ORGANIC

[2]

Capon B.M., 1976, Neighboring Group Participation

[3] S-benzoxazolyl (SBox) glycosides in oligosaccharide synthesis:: Novel glycosylation approach to the synthesis of β-D-glucosides, β-D-galactosides, and α-D-mannosides [J].