Doubly carbon-branched pentoses: synthesis of both enantiomers of 2.4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose using only acetonide protection

Journal article

An acetonide is the only protecting group used in the synthesis of both the enantiomers of 2,4-di-C-methyl arabinose and 2-deoxy-2,4-di-C-methyl arabinose via the enantiomeric 3-C-methyl-l-erythronolactone [from 2-C-methyl-d-ribono-lactone or d-ribose] and 3-C-methyl-d-erythronolactone [from d-tagatose or l-ribose]. NMR studies on unprotected C-methyl arabinoses show that methyl branching significantly affects the ratios of pyranose and furanose forms present in aqueous solution. © 2009 Elsevier Ltd. All rights reserved.

Authors: Booth, K; Jenkinson, S; Best, D; Fernandez Nieto, F; Estevez, R

• Publication status: Published
• Journal: TETRAHEDRON LETTERS
• Volume: 50
• Issue: 36
• Pages: 5088-5093
• Publication date: 2009-09-09
• DOI: 10.1016/j.tetlet.2009.06.098
• ISSN: 0040-4039
• Language: English