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协同布朗斯特酸型有机催化的立体选择性脱氧糖合成。

Cooperative Brønsted Acid-Type Organocatalysis for the Stereoselective Synthesis of Deoxyglycosides.

机构信息

School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, United Kingdom.

出版信息

J Org Chem. 2017 Jan 6;82(1):407-414. doi: 10.1021/acs.joc.6b02498. Epub 2016 Dec 22.

Abstract

A practical approach for the α-stereoselective synthesis of deoxyglycosides using cooperative Brønsted acid-type organocatalysis has been developed. The method is tolerant of a wide range of glycoside donors and acceptors, and its versatility is exemplified in the one-pot synthesis of a trisaccharide. Mechanistic studies suggest that thiourea-induced acid amplification of the chiral acid via H-bonding is key for the enhancement in reaction rate and yield, while stereocontrol is dependent on the chirality of the acid.

摘要

已开发出一种使用协同 Brønsted 酸型有机催化的α-立体选择性合成去氧糖苷的实用方法。该方法对各种糖苷供体和受体具有耐受性,其多功能性在一锅法合成三糖中得到了例证。机理研究表明,硫脲通过氢键诱导手性酸的酸增强是提高反应速率和产率的关键,而立体控制取决于酸的手性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/56c3/5309864/babb88569dd4/jo-2016-02498c_0001.jpg

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