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

Journal article

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. © 2009 Elsevier Ltd. All rights reserved.

Authors: Jenkinson, S; Booth, K; Estevez Reino, A; Horne, G; Estevez, R

• Publication status: Published
• Journal: TETRAHEDRON-ASYMMETRY
• Volume: 20
• Issue: 20
• Pages: 2357-2367
• Publication date: 2009-10-20
• DOI: 10.1016/j.tetasy.2009.08.029
• EISSN: 1362-511X
• ISSN: 0957-4166
• Language: English