Phosphorylated sugars. Part XIII. A new synthesis of D-arabinose 5-(dilithium phosphate)

Abstract

Phosphorylation of 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-D-glucofuranose with dipotassium hydrogen phosphate yields the corresponding 6-phosphate, which, after acidic hydrolysis and periodate cleavage between C-1 and C-2, gives the stable 2-O-benzyl-D-arabinofuranose 5-phosphate. Removal of the benzyl group by hydrogenolysis affords the title compound. In view of the known instability of pentose 5-phosphates D-arabinose 5-phosphate should be stored as its 2-O-benzyl derivative.