Synthesis of D-glycero-D-gulo-heptose, D-glycero-D-ido-heptose, and 2-deoxy-D-gluco-heptose from D-glucose

Abstract

D-Glucose was condensed with nitromethane to yield 1-deoxy-1-nitro-D-glycero-D-ido-heptitol and 1-deoxy-1-nitro-D-glycero-D-gulo-heptitol which were converted via the Nef reaction to D-glycero-D-ido-heptose and D-glycero-D-gulo-heptose respectively. The acetylated 1-deoxy-1-nitro-D-glycero-(D-ido- and D-gulo-)-heptitols were converted to 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-D-gluco-hept-1-enitol and reduction of this derivative afforded 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-D-gluco-heptitol which underwent the Nef reaction to give 2-deoxy-D-gluco-heptose.