Title of article :
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
Author/Authors :
Victoria Booth، نويسنده , , K. and Jenkinson، نويسنده , , Sarah F. and Best، نويسنده , , Daniel and Nieto، نويسنده , , Fernando Fernلndez and Estévez، نويسنده , , Ramَn J. and Wormald، نويسنده , , Mark R. and Weymouth-Wilson، نويسنده , , Alexander C. and Fleet، نويسنده , , George W.J.، نويسنده ,
Abstract :
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.
