通过分子内氧杂-Michael 反应和 Pummerer 重排合成修饰的甲基呋喃糖苷。

Synthesis of modified methyl furanosides by intramolecular oxa-Michael reaction followed by Pummerer rearrangement.

机构信息

Laboratoire de Synthèse Organique, CNRS UMR 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France.

出版信息

J Org Chem. 2010 May 7;75(9):3129-32. doi: 10.1021/jo100241e.

PMID:20384360

Abstract

A new method is described for the synthesis of ribofuranoses modified at the C3 and C5 positions. The key step is an intramolecular oxa-Michael reaction on a vinyl sulfoxide to install the C2 hydroxy group. The methyl furanosides are obtained by Pummerer rearrangement of the sulfoxide into the corresponding aldehyde, acidic deprotection of the benzylidene acetal, and cyclization.

摘要

本文描述了一种在 C3 和 C5 位置修饰核糖的新方法。关键步骤是在乙烯砜上进行分子内的氧杂迈克尔反应，以引入 C2 羟基。通过将砜转化为相应的醛、脱保护苯亚甲基缩醛和环化，得到甲基呋喃糖苷。