Glycosylation of a Ketone with an O-Glycosyl Trichloroacetimidate Provides an Enol Glycoside

Organic Letters
Xianglai LiuNing Ding

Abstract

An enol-type glycosylation reaction has been investigated. Enol glycosides can be obtained from the reaction between O-glycosyl trichloroacetimidates and the corresponding ketones promoted by an acid. The enol glycosides derived from cyclic ketones can be afforded efficiently and isolated in good yield, while those from acyclic ketones are prepared in low conversion or are too labile for isolation. Further studies on different glycosyl donor types indicate that only the O-glycosyl trichloroacetimidate works well as a donor for enol glycosylation.

References

May 1, 1994·Chemical & Pharmaceutical Bulletin·S SaitoY Sasaki
Feb 1, 2002·Organic Letters·Sean Handerson, Marcel Schlaf
Aug 15, 2002·Journal of the American Chemical Society·Yongda ZhangTomislav Rovis
Oct 12, 2002·Organic Letters·Charng-Sheng TsaiLee-Chiang Lo
Jul 15, 2006·The Journal of Organic Chemistry·Jialong YuanHolger Frauenrath
Oct 31, 2012·The Journal of Organic Chemistry·Haishen Yang, Pengfei Wang
Jun 13, 2015·Natural Product Reports·You YangBiao Yu
Mar 25, 2016·Bioconjugate Chemistry·Hiroyuki MatsuzakiYasuteru Urano

❮ Previous
Next ❯

Related Concepts

Related Feeds

Cardiac Glycosides

Cardiac glycosides are a diverse family of naturally derived compounds that bind to and inhibit na+/k+-atpase. Discover the latest research on cardiac glycosides heres.