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

Heike Wächtler; Dilver Peña Fuentes; Dirk Michalik; Martin Köckerling; Alexander Villinger; Udo Kragl; Quirino Arias Cedeño; Christian Vogel

doi:10.1055/s-0030-1260200

PAPER

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

Heike Wächtler^a,b, Dilver Peña Fuentes^a, Dirk Michalik^c, Martin Köckerling^a, Alexander Villinger^a, Udo Kragl^a, Quirino Arias Cedeño^d, Christian Vogel*^a
^a University of Rostock, Institute of Chemistry, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: christian.vogel@uni-rostock.de;
^b Agilent Technologies, Hewlett-Packard-Str. 8, 76337 Waldbronn, Germany
^c Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
^d Universidad de Granma, Carretera Manzanillo Km. 17.5, Bayamo Granma, Cuba

Abstract

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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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Referenzen

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