Synthesis 2018; 50(19): 3927-3930
DOI: 10.1055/s-0036-1591595
paper
© Georg Thieme Verlag Stuttgart · New York

An Expeditious Synthesis of 1-Thiotrehalose

Damien Tardieu
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, 25 rue Becquerel, 67000 Strasbourg, France   Email: philippe.compain@unistra.fr
,
Maria F. Céspedes Dávila
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, 25 rue Becquerel, 67000 Strasbourg, France   Email: philippe.compain@unistra.fr
,
Damien Hazelard
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, 25 rue Becquerel, 67000 Strasbourg, France   Email: philippe.compain@unistra.fr
,
Philippe Compain*
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, 25 rue Becquerel, 67000 Strasbourg, France   Email: philippe.compain@unistra.fr
› Author Affiliations
This work was supported by the CNRS, the University of Strasbourg and a doctoral fellowship from the French Department of Research to D.T.
Further Information

Publication History

Received: 19 April 2018

Accepted after revision: 24 May 2018

Publication Date:
12 July 2018 (online)


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.

Supporting Information

 
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