An Expeditious Synthesis of 1-Thiotrehalose

Damien Tardieu; Maria F. Céspedes Dávila; Damien Hazelard; Philippe Compain

doi:10.1055/s-0036-1591595

Synthesis, Table of Contents

Synthesis 2018; 50(19): 3927-3930
DOI: 10.1055/s-0036-1591595

paper

An Expeditious Synthesis of 1-Thiotrehalose

Authors

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

Abstract

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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.

Key words

glycomimetics - thio-sugars - anhydro sugars - domino reaction - ring-opening

Full Text

References

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Supplementary Material

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