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Synlett 2009(16): 2609-2612  
DOI: 10.1055/s-0029-1217956
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Properly Protected Sphingosine Acceptor for Helferich Glycosylation

Mario Michieletti, Laura Sillani, Luigi Panza*
Università degli Studi del Piemonte Orientale ‘Amedeo Avogadro’, Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Via Bovio, 6, 28100, Novara, Italy
Fax: +39(0321)375821; e-Mail: luigi.panza@pharm.unipmn.it;
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Publication History

Received 30 June 2009
Publication Date:
04 September 2009 (online)

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Abstract

The synthesis and some examples of glycosylations of a properly protected sphingosine is presented. This compound is suitable for the preparation of glycosphingolipids. It has been used for the synthesis of α-mannosylceramide and sulfatide exploiting the anchimeric assistance to address the stereochemistry of the glycosidic bond.

Key words

glycosylations - carbohydrates - synthesis - sphingolipids - heterocycles

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