Download PDF
Synthesis 1996; 1996(12): 1451-1454
DOI: 10.1055/s-1996-4407
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Addition of an Apiosyl Radical to Activated Olefins - Synthesis of C-Apiosyl Compounds

Martina Drescher, Friedrich Hammerschmidt*
  • *Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

3’-O-Benzoyl-2,3-O-isopropylidene-D-apio-β-D-furanosyl bromide (8), prepared in two steps from 2,3-O-isopropylidene-D-apio-β-D-furanose (6), was reacted with tris(trimethylsilyl)silane/AIBN in the presence of an excess of a variety of activated olefins such as dimethyl maleate, methyl acrylate, acrylonitrile, methyl vinyl ketone, crotonaldehyde, cyclopent-2-enone, and cyclohex-2-enone to afford the corresponding C-apiosides 10 having β-configuration.

C-Apiosides 10a-g are prepared from apiosyl bromide 8 via (TMSi)3SiH/AIBN induced radical addition to activated olefins 9a-g