摘要 |
A process for the production of (+/-)3-deazaaristeromycin, which is also known as (+/-)-4-amino-1-[(1 alpha , 2 beta , 3 beta , 4 alpha )-2,3-dihydroxy-4-(hydroxymethyl)-cyclopentyl]imidazo[4,5-c]pyridine, which comprises: (1) reacting 2,4-dichloro-3-nitropyridine with (+/-)(1,4/2,3)-4-amino-2,3-dihydroxy-1-cyclopentanemethanol to give (+/-)-(1,4/2,3)-4-(3-nitro-2-chloro-4-pyridylamino)-2,3-dihydroxy-1-cy clopentanemethanol (compound II); (2) subsequently reducing compound II to (+/-)-(1,4/2,3)-4(3-amino-2-chloro-4-pyridylamino)-2,3-dihydroxy-1-cyc lopentanemethanol (compound III); (3) acid catalyzed cyclization of compound III to (+/-)-4-chloro-1-(1 alpha , 2 beta , 3 beta , 4 alpha )-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl)imidazo[4,5-c]pyridine (compound IV); (4) displacing the chloro group of compound IV to produce (+/-)-4-hydrazino-1-(1 alpha , 2 beta , 3 beta , 4 alpha )-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl)-imidazo[4,5-c]pyridine (compound V); (5) cleaving said hydrazino compound V to produce (+/-)-4-amino-1-[(1 alpha , 2 beta , 3 beta , 4 alpha )-2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]imidazo[4,5-c]-pyridine (compound VI).
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