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2 amino 7 beta d arabinofuranosyl 4 methoxy 7h pyrrolo 2 3 d pyrimidine a facile preparation and anomerization of a 7 deaza purine nucleoside



2 amino 7 beta d arabinofuranosyl 4 methoxy 7h pyrrolo 2 3 d pyrimidine a facile preparation and anomerization of a 7 deaza purine nucleoside



Carbohydrate Research 118: 29-36



Phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine with 2,3,5-tri-O-benzyl-D-arabinofuranosyl bromide in benzene-50% aqueous NaOH tetrabutylammonium hydrogensulfate gave 2 anomeric glycosylation products (1 and 3). Removal of the benzyl groups from 1 and 3, respectively, with BCl3 yielded 2-amino-7(.alpha.- and .beta.-D-arabinofuranosyl)-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (4 and 2). Treatment of 2 and 4 with 2M HCl under N2 caused anomerization and demethylation without glycosylic cleavage and reflected the extraordinary stability of pyrrolol[2,3-d]pyrimidine nucleosides towards hydrolysis. The conversion of 2 and 4 into ara-7-deazaguanosine or its .alpha. anomer was accomplished with anhydrous acid.

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