D-glycero-D-gulo-HEPTONO-1,4-LACTONE AS A PRECURSOR FOR THE SYNTHESIS OF DEOXYHEPTONOLACTONES AND ANHYDROHEPTONOLACTONES

Article abstract of DOI:10.1016/0008-6215(88)85102-4

Hydrogenolysis of D-glycero-D-gulo-heptono-1,4-lactone penta-acetate gave 3-deoxy-D-gluco-heptonolactone tetra-acetate, which was converted easily into methyl 3-deoxy-D-gluco-heptonate and, thence, into 7-bromo-3,7-dideoxy- and 3,7-dideoxy-D-gluco-heptono-1,4-lactone.Reaction of D-glycero-D-gulo-heptono-1,4-lactone (4a) with hydrogen bromide-acetic acid gave 2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-1,4-lactone (5), hydrogenolysis of which gave 7-bromo-2,7-dideoxy- (7), 2,7-dideoxy- (8), or 7-bromo-2,3,7-trideoxy-heptono-1,4-lactone (9), depending on the conditions.When 5 was heated in water, it gave 2,5:4,7-dianhydro-D-glycero-D-gulo-heptonic acid.Reaction of 4a with formic acid in hydrogen fluoride yielded a mixture of 3,6-anhydro-L-glycero-D-gulo-heptono-1,4-lactone and 3,7-anhydro-D-glycero-D-gulo-heptono-1,4-lactone.Similar treatment converted 7 and 8 into 3,6-anhydrides.