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Synthesis of higher carbon sugars. Unexpected rearrangement of higher sugar allylic alcohols

Sławomir Jarosz ,  Agnieszka Gajewska 

Instytut Chemii Organicznej Polskiej Akademii Nauk (ICHOPAN), Kasprzaka 44/52, Warszawa 01-224, Poland

Abstract

Higher carbon sugars containing more than 10 carbon atoms in the chain, although occuring very rarley in nature , are important components of some antibiotics. Methodology developed in our laboratory allows to obtain rather easily precursors of type 3, higher sugar enones substituted at both terminal positions with monosaccharide sub-units [1].

Enone 3 was obtained in the reaction of phosphonate 1 with aldehyde 2. Reduction of the carbonyl function provided two stereoisomeric allylic alcohols with the R-isomer predominating. Attempts to invert the configuration at the carbinol center failed and the rearranged compound 6 was obtained as the sole product in this process.

[1] S. Jarosz, J. Carbohydr. Chem., 2001, 20, 93: S. Jarosz, Curr. Org. Chem., 2008, w druku

 

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Related papers

Presentation: Oral at VI Multidyscyplinarna Konferencja Nauki o Leku, by Sławomir Jarosz
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2008-02-22 08:58
Revised:   2009-06-07 00:48