An Expeditious Synthesis of 1-Thiotrehalose

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

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