An efficient route to optically active inositol derivatives via the resolution of myo-inositol 1,3,5-orthoformate: a short synthesis of D-myo-inositol-4-phosphate

摘要

An efficient method for the resolution of myo-inositol 1,3,5-orthoformate has been developed. The triol, 1 was converted to diastereomers via reaction with (S)-O-acetylmandeloyl chloride. Conditions were optimized for a diastereomeric ratio of 7:3. Both the diastereomers could be separated by column chromatography. The absolute configurations of the diastereomers were determined by converting the less polar diastereomer to the known L-2,4-di-O-benzyl-myo-inositol. The utility of the resolved derivatives is illustrated by a short and efficient synthesis of D-myo-inositol-4-phosphate in four steps from myo-inositol. (C) 2004 Elsevier Ltd. All rights reserved.