A new synthesis of 3-amino-3-deoxy-α-D-mannopyranosyl 3-amino-3-deoxy-α-D-mannopyranoside, a potential antituberculous agent

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Abstract
A practical, four-step synthesis of the title compound starting from 2-O-benzyl-4,6-O-benzylidene-α-D-altropyranosyl 2-O-benzyl-4,6-O-benzylidene-α-D-altropyranoside is described. Trifluoromethylsulfonylation followed by azide displacement furnished the corresponding α-D-manno,α-D-manno 3,3′-diazido-3,3′-dideoxy derivative, and subsequent hydrolytic deacetalation, followed by catalytic transfer hydrogenolysis to simultaneously reduce the azido groups and cleave the benzyl ether groups, gave the title disaccharide in 30% overall yield. As preceding work had provided the blocked starting disaccharide in a sequence of four facile operations departing from commercial α,α-trehalose (overall yield, 53%), the title compound can now be prepared conveniently on a multigram scale.