Peracetylated β-Allyl
C-Glycosides of d-Ribofuranose and 2-Deoxy-d-ribofuranose in the Chemical Literature:
Until Now, Mirages in the Literature

Heike Otero Martinez; Helmut Reinke; Dirk Michalik; Christian Vogel

doi:10.1055/s-0029-1216794

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Synthesis 2009(11): 1834-1840
DOI: 10.1055/s-0029-1216794

PAPER

Peracetylated β-Allyl C-Glycosides of d-Ribofuranose and 2-Deoxy-d-ribofuranose in the Chemical Literature: Until Now, Mirages in the Literature

Heike Otero Martinez^a,1, Helmut Reinke^a, Dirk Michalik^b, Christian Vogel*^a
^a Institute of Chemistry, University of Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: christian.vogel@uni-rostock.de;
^b Leibniz Institute for Catalysis, University of Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

Further Information

Publication History

Received 27 January 2009
Publication Date:
12 May 2009 (online)

Abstract
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Abstract

The peracetylated β-allyl C-glycosides of d-ribofuranose (8) and 2-deoxy-d-ribofuranose (13) were stereoselectively prepared via the isopropylidene derivatives 3 and 4. These reactions represent what are, to the best of our knowledge, the first preparation of these apparently simple derivatives whose structures were carefully proved by NMR and X-ray investigations. Publications which allegedly described the synthesis of 8 and 13 were critically examined.

Key words

allylation - glycosylation - C-glycosides - nucleosides - stereoselectivity

References

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1

Present address: University Karlsruhe, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131, Karlsruhe, Germany.

21

Crystallographic data for the structural analysis has been deposited with the Cambridge Crystallographic Data Centre under CCDC No. 717935 and 717936 for compounds 6 and 18, respectively. Copies of this information may be obtained free of charge from: The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ UK. Fax: +44(1223)336033 or via
e-mail: deposit@ccdc.cam.ac.uk or
http://www.ccdc.cam.ac.uk.