L-ristosamine 和 L-表-daunosamine 糖苷的短高效合成。

A short and highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides.

机构信息

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

出版信息

Org Lett. 2011 Feb 18;13(4):652-5. doi: 10.1021/ol102891t. Epub 2011 Jan 18.

DOI:10.1021/ol102891t

PMID:21244045

Abstract

A highly efficient synthesis of L-ristosamine and L-epi-daunosamine glycosides via BF(3)·OEt(2) promoted tandem hydroamination/glycosylation of 3,4-di-O-acetyl-6-deoxy-L-glucal and L-galactal has been developed. The new method proceeds in a completely stereocontrolled manner within a short reaction time. Preparation of a library of L-ristosamine and L-epi-daunosamine glycosides with potential biochemical applications, by varying each component, exemplified the generality of the reaction.

摘要

通过 BF(3)·OEt(2) 促进的 3,4-二-O-乙酰基-6-去氧-L-吡喃葡萄糖和 L-半乳糖的串联氢胺化/糖苷化反应，高效合成了 L-ristosamine 和 L-epi-daunosamine 糖苷。该新方法在短反应时间内以完全立体控制的方式进行。通过改变每个组成部分，制备了具有潜在生化应用的 L-ristosamine 和 L-epi-daunosamine 糖苷文库，证明了反应的通用性。