An efficient synthesis of acyclic N7-and N9-adenine nucleosides via alkylation with secondary carbon electrophiles to introduce versatile functional groups at the C-1 …

…, VS Kumar, TH Lin, Y El-Kattan, A Ghosh…

Index: Kotian, Pravin L.; Kumar, V. Satish; Lin, Tsu-Hsing; El-Kattan, Yahya; Ghosh, Ajit; Wu, Minwan; Cheng, Xiaogang; Bantia, Shanta; Babu, Yarlagadda S.; Chand, Pooran Nucleosides, Nucleotides and Nucleic Acids, 2006 , vol. 25, # 2 p. 121 - 140

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Citation Number: 4

Abstract

The introduction of versatile functional groups, allyl and ester, at the C-1 position of the acyclic chain in acyclic adenine nucleosides was achieved for the first time directly by alkylation of adenine and N6-protected adenine. Thus, the C-1′-substituted N9-adenine acyclic nucleoside, adenine-9-yl-pent-4-enoic acid ethyl ester (11), was prepared by direct alkylation of adenine with 2-bromopent-4-enoic acid ethyl ester (6), while the ...