Synthesis of C2-Methylene Glycitols from 1,2-Cyclopropanated Sugars: En Route to Iminosugar Analogues

Abstract

C2-Methylene glycitols were synthesized in three steps by halonium ion mediated solvolytic ring opening of 1,2-cyclopropanated sugars, dehydrohalogenation using potassium carbonate in aqueous acetonitrile, and reduction with sodium borohydride. The generality of the methodology was evaluated by applying it to a series of 1,2-cyclopropanated pyranoses as well as furanoses to give the corresponding C2-methylene glycitol derivatives. Furthermore, the obtained glycitols were converted into 1-deoxy-C2-methylene iminosugar derivatives.

Key words

azasugars - carbohydrates - electrophilic addition - piperidines - cyclization

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