Phosphorylated sugars. Part XIV. Synthesis of D-glycero-L-manno-heptose 7-(dihydrogen phosphate)

Abstract

Detritylation of 1,2,3,4,6-penta-O-benzoyl-7-O-trityl-β-D-glycero-L-manno-heptose with hydrobromic acid in acetic acid, followed by phosphorylation and removal of the protecting groups, affords D-glycero-L-manno-heptose 7-phosphate. A similar sequence of reactions starting with 1,2,3,4,6-penta-O-acetyl-7-O-trityl-D-glycero-L-manno-heptose gave the same phosphate, showing that detritylation of this heptose derivative is not accompanied by an acid-catalysed acetyl migration similar to that observed previously in detritylation of 1,2,3,4,6-penta-O-acetyl-7-O-trityl-D-glycero-D-galacto-heptose.