1,4-diamino-1,4-dideoxy-d-galactitol and 1,5-diamino-1,5-dideoxy-l-altritol☆

Add time:09/10/2019    Source:sciencedirect.com

The mesyloxy group of 1-azido-1-deoxy-4-O-mesyl-d-glucitol could be displaced by azide, in the 2,3:5,6-di-O-isopropylidene derivative 4 or the 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. Reduction of the corresponding deprotected diazides afforded the title compounds.

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