通过费里尔型重排加速外糖基的立体选择性糖基化反应。

Stereoselective glycosylation of exo-glycals accelerated by Ferrier-type rearrangement.

作者信息

Lin Hui-Chang, Yang Wen-Bin, Gu Yu-Feng, Chen Chen-Yin, Wu Chung-Yi, Lin Chun-Hung

机构信息

Institute of Biological Chemistry, Academia Sinica, No. 128, Academia Road Section 2, Nan-Kang, Taipei, 11529, Taiwan.

出版信息

Org Lett. 2003 Apr 3;5(7):1087-9. doi: 10.1021/ol034130z.

DOI:10.1021/ol034130z

PMID:12659580

Abstract

[reaction: see text] Owing to the driving force of the Ferrier-type rearrangement, the exo-glycals are highly reactive with various alcohols to afford glycosides and glycoconjugates with exclusive alpha-configuration. The resulting vinyl group in these glycosylation products can be further elaborated for general applications, including the synthesis of spiro derivatives and glycosylation of 2-ketoaldonic acids.

摘要

[反应：见正文] 由于费里尔型重排的驱动力，外型糖苷在与各种醇反应时具有很高的反应活性，可生成具有单一α构型的糖苷和糖缀合物。这些糖基化产物中生成的乙烯基可进一步用于一般应用，包括螺环衍生物的合成和2-酮醛糖酸的糖基化。