铑（II）卡宾促进碳水化合物端基 C-H 键的活化：一种对映选择性构建 α-和 β-酮吡喃糖苷的方法。

Rh(II) carbene-promoted activation of the anomeric C-H bond of carbohydrates: a stereospecific entry toward α- and β-ketopyranosides.

机构信息

Laboratoire de Chimie Thérapeutique (UMR CNRS 8638), Université Paris Descartes, Faculté des Sciences Pharmaceutiques et Biologiques, 4, avenue de l'Observatoire, 75006 Paris, France.

出版信息

J Am Chem Soc. 2010 Nov 10;132(44):15477-9. doi: 10.1021/ja1054065.

DOI:10.1021/ja1054065

PMID:20961097

Abstract

In this communication we report a new strategy toward ketopyranosides based on a carbene-mediated activation of the anomeric C-H bond of carbohydrates. By forming a new carbon-carbon bond after a glycosylation step, this approach enables the preparation of both α- and β-ketopyranosides from advanced precursors.

摘要

在本通讯中，我们报告了一种基于卡宾介导的碳水化合物端基 C-H 键活化的新型酮吡喃糖苷合成策略。通过在糖苷化步骤后形成新的碳-碳键，该方法能够从高级前体中制备α-和β-酮吡喃糖苷。