Approach to higher carbon sugars functionalized at both terminal positions

Model study on the synthesis of higher carbon sugars using the phosphonate approach is presented. A C-7 sugar phosphonate was reacted with a C-5 sugar aldehyde under mild phase-transfer conditions to afford the C-12-alpha, beta-unsaturated ketone. Proper functionalization of the internal C-3-carbon...

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Bibliographic Details
Published inPolish journal of chemistry Vol. 81; no. 11; pp. 1949 - 1957
Main Authors Jarosz, S., Gajewska, A.
Format Journal Article
LanguageEnglish
Published WARSAW Polish Chemical Soc 01.11.2007
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Wittig-type reaction
WITTIG
MONOSACCHARIDES
1ST SYNTHESIS
ACIDS
cis-hydroxylation
higher carbon sugars
selective hydrolysis
stereoselective reduction
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Summary:Model study on the synthesis of higher carbon sugars using the phosphonate approach is presented. A C-7 sugar phosphonate was reacted with a C-5 sugar aldehyde under mild phase-transfer conditions to afford the C-12-alpha, beta-unsaturated ketone. Proper functionalization of the internal C-3-carbon bridge provided derivative suitable for differentiation at both 'ends', thus allowing to introduce the desired functionality either at the C- 1 or C-12 positions.
ISSN:0137-5083