The relayed introduction of alkylthio-groups into carbohydrate derivatives: a novel synthesis of amicetose

Abstract

The ethanethiolysis of 3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose gives ethyl 4-O-benzoyl-2,3,6-tri-S-ethyl-1,2,3,6-tetrathio-α-D-mannopyranoside as main product. The thio-groups are shown to be introduced first at C-1 and are then relayed as follows: C-1 → C-2 → C-3 → C-6. The tetrathio-compound affords a new route to the antibiotic sugar amicetose (2,3,6-trideoxy-D-erythro-hexose).