2008Organic & Biomolecular ChemistryRequires access

A direct and stereospecific approach to the synthesis of α-glycosyl thiols

Ravindra T. Dere, Yingxi Wang, Xiangming Zhu

Open publisher page 45 citations

Abstract

A new simple method for the synthesis of alpha-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded alpha-glycosyl thiols in very high yields and in a stereospecific way.

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What this paper is about

A new simple method for the synthesis of alpha-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded alpha-glycosyl thiols in very high yields and in a stereospecific way.

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Available abstract

A new simple method for the synthesis of alpha-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded alpha-glycosyl thiols in very high yields and in a stereospecific way.

Key concepts: Glycosyl, Stereospecificity, Chemistry, Trimethylsilyl, Sulfide, Ring (chemistry), Combinatorial chemistry, Catalysis

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