Synthesis of some methylated tetroses and pentoses

Abstract

Oxidation of 2,3-di-O-methyl-D-glucitol (≡ 4,5-di-O-methyl-L-gulitol) and 2,3-di-O-methyl-D-mannitol (≡ 4,5-di-O-methyl-D-mannitol) with an excess of periodate gave 2,3-di-O-methyl-L-threose and 2,3-di-O-methyl-D-erythrose, each characterized as the 2,4-dinitrophenylhydrazone. Borohydride reduction of the sugars gave 2,3-di-O-methyl-L-threitol and 2,3-di-O-methylerythritol characterized as their di-p-nitrobenzoates. Oxidation of the hexitols with 1 mole of periodate gave 3,4-di-O-methyl-L-xylose characterized as methyl 3,4-di-O-methyl-α-L-xylopyranoside and 3,4-di-O-methyl-D-arabinose identified as 3,4-di-O-methyl-D-arabonamide. 2-O-Methyl-D-erythritol (≡ 3-O-methyl-L-erythritol) and 1-O-methyl-D-threitol (≡ 4-O-methyl-D-threitol) were also prepared and characterized as the tri-p-nitrobenzoates.