De Novo Synthesis of Racemic 4-Deoxy-4,4-difluoro- and 2,4-Dideoxy-2,4,4-trifluorohexosides

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Abstract

A range of racemic 4-deoxy-4,4-difluorinated carbohydrates were prepared by using a diversity-oriented de novo synthesis starting with three commercially available two-carbon building blocks. A common gem-difluorinated glycal was prepared in 35 % yield in seven steps, from which five different 4-deoxy-4,4-difluoro- and 4-deoxy-2,4,4-trifluorohexopyranosides were accessed using well-established functional group manipulations.

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