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-.ALPHA.-D-glucopyranose.

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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(benzyloxycarbonylamino)-3,4,6-trideoxy-D-glucitol (23), which was then oxidized successively with periodate and chromium trioxide-acetic acid-pyridine to give 2,3,5-tris(benzyloxycarbonylamino)-2,3,5-trideoxy-D-arabono-1,4-lactone (25); this was further transformed into 2,3,5-trianimo-2,3,5-trideoxy-D-arabono-1,5-lactam (16).
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