通过交叉复分解反应实现亚氨基糖 C-糖苷构建模块的通用获取：通往糖缀合物模拟物的途径。

General access to iminosugar C-glycoside building blocks by means of cross-metathesis: a gateway to glycoconjugate mimetics.

作者信息

Godin Guillaume, Compain Philippe, Martin Olivier R

机构信息

Institut de Chimie Organique et Analytique, UMR-CNRS 6005, Université d'Orléans, rue de Chartres, BP 6759, 45067 Orléans Cedex 2, France.

出版信息

Org Lett. 2003 Sep 4;5(18):3269-72. doi: 10.1021/ol035117h.

DOI:10.1021/ol035117h

PMID:12943404

Abstract

[reaction: see text] Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest.

摘要

[反应：见正文] 报道了α-1-C-烯丙基-1-脱氧野尻霉素衍生物7a、b与各种官能化烯烃在Grubbs催化剂3介导下的交叉复分解反应。这些反应的产率合理至非常高，且具有出色的E/Z选择性。该方法能够高效、汇聚式地合成在糖苷配基中具有高度结构多样性的亚氨基糖C-糖苷，为多种具有生物学意义的新型糖缀合物模拟物开辟了道路。