Conversion of D-xylose to protected D-lyxose derivatives and to D-lyxose, via the corresponding 1,2-anhydride

Abstract

Acid hydrolysis of 3,5-di-O-benzyl-1,2-O-cyclohexylidene-α-D-xylofuranose gave the corresponding lactol, which was subsequently converted to the 3,5-di-O-benzyl-2-O-mesyl-D-xylofuranose. This compound readily reacted with sodium methoxide, sodium benzylate or sodium hydroxide (presumably via the corresponding 1,2-anhydride) to give the protected D-lyxofuranosides. These compounds were finally converted to methyl α-D-lyxopyranoside or to D-lyxose. Copyright (C) 1999 Elsevier Science Ltd.