Preparation of ethyl 2-azido-2-deoxy-1-thio-beta-mannopyranosides, and their rearrangement to 2-S-ethyl-2-thio-beta-D-mannopyranosylamines

Abstract

The synthesis of ethyl 2-azido-2-deoxy-1-thio-ß-d-mannopyranosides, starting from appropriate synthons with gluco configuration, via SN2 substitution at C(2), and their rearrangement to 2-S-ethyl-2-thio-ß-d-mannopyranosylamines are presented.

Keywords

• carbohydrates
• D-mannosamine
• thioglycosides
• ste­reoselective synthesis
• intramolecular rearrangements