Synthesis of the dideoxynucleosides" ddC" and" CNT" from glutamic acid, ribonolactone, and pyrimidine bases

M Okabe, RC Sun, SYK Tam, LJ Todaro…

文献索引：Okabe, Masami; Sun, Ruen-Chu; Tam, Steve Y.-K.; Todaro, Louis J.; Coffen, David L. Journal of Organic Chemistry, 1988 , vol. 53, # 20 p. 4780 - 4786

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被引用次数: 198

摘要

2, 3-Dideoxyribose in suitably protected form was prepared from glutamic acid and coupled with silylated cytosine to give a mixture of the a-and P-anomers of 2', 3'-dideoxycytidine. The anomer ratio depended on the Lewis acid used in the coupling, with EtA1C12 favoring the@- anomer ddC, a potent anti-HIV drug. Conjugate addition of cyanide to a 4-[(silyloxy) methyl] butenolide prepared from D-ribonolactone gave a mixture of (racemic) a-and@-3- ...