Phosphorylated sugars. Part XVIII. Synthesis of D-glycero-D-gulo-heptose 4-(dihydrogen phosphate)

Abstract

Condensation of benzyl β-D-glycero-D-gulo-heptopyranoside with cyclohexanone gave the 2,3:6,7-di-O-cyclohexylidene derivative, the structure of which was established by mass spectrometry of its benzoate. Phosphorylation of the dicyclohexylideneheptoside, followed by acidic hydrolysis to remove the cyclohexylidene groups, yielded the benzyl heptoside 4-phosphate, which was de-O-benzylated by hydrogenolysis.