Synthesis of 4′-methoxyadenosine and related compounds |
| |
Authors: | Colin M Richards Julien PH Verheyden John G Moffatt |
| |
Institution: | Institute of Molecular Biology, Syntex Research, Palo Alto, California 94304 U.S.A. |
| |
Abstract: | Addition of iodine and methanol to N6,N6-dibenzoyl-9(2,3-O-carbonyl-5-deoxy-β-d-erythro-pent-4-enofuranosyl)adenine (4) selectively gives N6,N6-dibenzoyl-2′,3′-O-carbonyl-5′-deoxy-5′-iodo-4′-methoxyadenosine (5). Compound 5 can be converted into 4′-methoxyadenosine via hydrolysis of the carbonate followed by benzoylation, displacement of the 5′-iodo function by benzoate ion, and hydrolysis with ammonia. Configurational assignments are based upon comparisons of 1H- and 13C-n.m.r. spectra with those of previously characterised analogues in the uracil series and by borate electrophoresis. Intermediates in the above scheme have also been converted into 5′-amino-5′-deoxy-4′-methoxyadenosine, 4′-methoxy-5′-O-sulfamoyladenosine, and ethyl 4′-methoxyadenosine-5′-carboxylate, each of which is a 4′-methoxy analogue of biologically active derivatives of adenosine. |
| |
Keywords: | To whom correspondence should be addressed |
本文献已被 ScienceDirect 等数据库收录! |
|