Benzyl-2,4-Diacetamido-2, 4,6-Tri-Deoxy-α(β) -D-Galactopyranoside

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Abstract
Benzyl-2,4-diacetamido-2,4,6-trideoxy-α(β)-D-galactopyranoside 6c was synthesized from l,6-anhydro-2,3-O-(4-methoxybenzylidene)-β-D-mannopyranose la. The azide group at C-4, which is a precursor for the acetamido function, was introduced by substitution of the 4-O-triflate group with lithium azide. After regioselective oxidative acetal ring opening the other C-2 azide function was obtained by the same substitution procedure. Acetolysis of the 1,6-anhydro bridge and α(β)-coupling with benzyl alcohol gave the 2,4-diazido derivative 4b. After base treatment the azide groups were reduced and subsequently acetylated. Selective protection of the primary hydroxyl by the phenyl thionocar-bonyl group followed by reduction afforded the title compound.

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