SYNTHETIC APPROACH TO 2,3,5-TRIAMINO-2,3,5-TRIDEOXY-D-ARABONIC ACID DERIVATIVES FROM 3,4,6-TRIAZIDO-3,4,6-TRIDEOXY-1,2-O-ISOPROPYLIDENE-α-D-GLUCOPYRANOSE

3,6-Diazido-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose was converted into the corresponding derivative of α-D-glucopyranose, which was transformed into 3,4,6-triazido-3,4,6-trideoxy-1,2-O-isopropylidene-α-D-glucopyranose (7) through the sequence of reactions involving displacement of sulfonate ester function with benzoate, followed by debenzoylation, sulfonylation, and nucleophilic substitution. Hydrogenolysis of 7 afforded the corresponding triamino derivative 8. The tri-N-benzyloxycarbonyl derivative of 8 was O-deisopropylidenated and oxidized with periodate to afford the piperidinose derivative 11, deformylation of which yielded 2,3,5-tris(benzyloxycarbonylamino)-2,3,5-trideoxy-D-arabinopyranose (13). “Pfitzner-Moffatt” oxidation of 11 failed to give the corresponding lactam 15. Condensation of the 6-N-benzyloxycarbonyl derivative of 8 (18) with cyanogen bromide afforded the cyclic guanidine derivative (20) hydrobromide. The triazido derivative 7 was converted into 3,4,6-tris(benzyloxycarbonyla...