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

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: [phone] or via
e-mail: [e-mail] or
http://www.ccdc.cam.ac.uk.