Synthesis of Cyclopropanated Dimethyl Mercaptal Sulfoxide Pyranoses from Epoxytriflate Pyranosides and Methyl Methylthiomethyl Sulfoxide

Stereospecifically cyclopropanated sugar deriva­ tives are not only interesting from their biological point of view, but they can also serve as templates for the synthesis of natural products using the chiron approach [1]. The previous successes in the synthesis of a number of cyclopropanated sugar derivatives via diplacement of the triflyl group [2] promoted us to investigate a similar reaction with a carbanion derived from methyl methylthio­ methyl sulfoxide [3] for the synthesis of 2,3-cyclopropanated dimethyl mercaptal sulfoxide sugars.