An Expeditious Synthesis of 1-Thiotrehalose-Reference-Cited by-同舟云学术

An Expeditious Synthesis of 1-Thiotrehalose

Published:2018-07-12 Issue:19 Volume:50 Page:3927-3930
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Compain Philippe¹,Tardieu Damien¹,Céspedes Dávila Maria¹,Hazelard Damien¹

Affiliation:

1. Laboratoire d’Innovation Moléculaire et Applications (LIMA), Université de Strasbourg, Université de Haute-Alsace, CNRS (UMR 7042). Equipe de Synthèse Organique et Molécules Bioactives (SYBIO), Ecole Européenne de Chimie, Polymères et Matériaux

Abstract

A two-step synthesis of 1-thiotrehalose is reported. In the key TMSOTf-mediated double thioglycosylation step, the tri-O-benzyl 1,6-anhydro-D-glucose reactant behaves both as a glycosyl donor and a glycosyl acceptor precursor. In this highly convergent process, two carbon-sulfur bonds are created at the anomeric positions with a high level of stereocontrol.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0036-1591595.pdf

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