Carbon-branched carbohydrate chirons: synthesis of C-3 and C-4-branched sugar lactones derived from d-erythronolactone

Two carbon chain extensions using a Wittig reaction on both a 1-deoxy ribulose derivative and a C-2-branched erythrose derivative are reported. Subsequent dihydroxylation resulted in the synthesis of C-3 and C-4 methyl-branched sugar lactones, the useful synthetic building blocks. Control of the ste...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2009-10, Vol.20 (20), p.2357-2367
Main Authors: Jenkinson, Sarah F., Victoria Booth, K., Estévez Reino, Amalia M., Horne, Graeme, Estévez, Ramón J., Fleet, George W.J.
Format: Article
Language:English
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Summary:Two carbon chain extensions using a Wittig reaction on both a 1-deoxy ribulose derivative and a C-2-branched erythrose derivative are reported. Subsequent dihydroxylation resulted in the synthesis of C-3 and C-4 methyl-branched sugar lactones, the useful synthetic building blocks. Control of the stereoselectivity of both the Wittig reaction and the dihydroxylation is investigated, and 3- C-methyl and 4- C-methyl d-altrono-1,4-lactones and d-glucono-1,4-lactone and 4- C-hydroxymethyl- d-altrono-1,4-lactone were synthesised.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2009.08.029