A Versatile Approach to Alcohol, Aldehyde, Ketone and Amine Derivatives Starting from β-Allyl C-Glycosides of d-Ribofuranose and 2-Deoxy-d-ribofuranose

Abstract

An efficient preparative procedure is described, leading from β-allyl C-glycosides of d-ribofuranose to alcohols by a hydroboration-oxidation procedure. The corresponding aldehydes were obtained by Swern or Dess-Martin oxidation. Alternatively, two of the alcohols were mesylated to gain access to azides and amines. Treatment of the aldehydes with ethynylmagnesium bromide or phenylethynyllithium and consecutive oxidation of the diastereomeric­ alcohols provided the acetylenic ketones in good to excellent yields. The obtained derivatives serve as important intermediates for the synthesis of various heterocyclic systems.

Key words

ribofuranose - C-nucleosides - hydroboration - oxidation - amines - aldehydes - alkynes

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