1,4-DIAMINO-1,4-DIDEOXY-D-GALACTITOL AND 1,5-DIAMINO-1,5-DIDEOXY-L-ALTRITOL

Article abstract of DOI:10.1016/S0008-6215(00)90097-1

The mesyloxy group of 1-azido-1-deoxy-4-O-mesyl-D-glucitol could be displaced by azide, in the 2,3:4,5-di-O-isopropylidene derivative 4 or tetraacetate, yielding, after removal of the protecting groups, 1,4-diazido-1,4-dideoxy-D-galactitol (7).The 2,3- (10( and 5,6-O-isopropylidene derivative (13) of 7 gave, on mesylation, the corresponding 5,6- (11) and 2,3-dimesylate (15), respectively.Treatment of 11 with hydrochloric acid yielded 3,6-anhydro-1,4-diazido-1,4-dideoxy-5-O-mesyl-D-galactitol, whereas 15 gave the corresponding 5,6-diol which was converted with base into 2,6-anhydro-1,4-diazido-1,4-dideoxy-3-O-mesyl-D-talitol.Cleavage of the 5,6-O-isopropylidene group of 4 gave 1-azido-1-deoxy-2,3-O-isopropylidene-4-O-mesyl-D-glucitol, which could be converted via the corresponding 4,5-epoxide into 1,5-diazido-1,5-dideoxy-2,3-O-isopropylidene-L-altritol (25).The 6-p-nitrobenzoates of 25 and 13 are derivatives suitable for the synthesis of sorbistin analogues.Reductionof the corresponding deprotected diazides afforded the title compound.