Synthesis of a c-nucleoside analog of the antibiotic cordycepin
Document Type
Article
Publication Date
1-1-1974
Abstract
A C-nucleoside analog of cordycepin, 6-amino-8-(3-deoxy-β-D-erythro-pentofuranosyl)purine (6), has been synthesized. 3-Deoxy-2,5-di-O-(p-nitrobenzoyl)- β-D-erythro-pentofuranosyl bromide reacted with mercuric cyanide in nitromethane to give 2,5-anhydro-4-deoxy-3,6-di-O-(p-nitrobenzoyl)-D-ribo-hexononitrile which, after acid hydrolysis and removal of the protecting groups, afforded 2,5-anhydro-4-deoxy-D-ribo-hexonic acid. Reaction of this acid with 4,5,6-triaminopyrimidine gave the corresponding amide, which was pyrolyzed to give compound 6. The mass- and n.m.r.-spectral data for the synthesized analog are quite similar to those of the natural antibiotic. © 1974.
Publication Title
Carbohydrate Research
Recommended Citation
El Khadem, H.,
&
El Ashry, E.
(1974).
Synthesis of a c-nucleoside analog of the antibiotic cordycepin.
Carbohydrate Research,
32(2), 339-348.
http://doi.org/10.1016/S0008-6215(00)82110-2
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/7220