An efficient regioselective synthesis of substituted purine analogues of guanosine and inosine

N Raju, RK Robins, MM Vaghefi

Index: Raju, Natarajan; Robins, Roland K.; Vaghefi, Morteza M. Journal of the Chemical Society, Chemical Communications, 1989 , # 2 p. 1769 - 1770

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Abstract

Condensation of 2-bromo-6-(4-nitrophenylethoxy) purine as the trimethylsilyl derivative (5a) with 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose, 1-O-acetyl-2, 3-di-O-benzoyl-5-diethoxy- phosphinyl-β-D-ribofuranose, and (2-acetoxythoxy) methyl bromide resulted in N9- regioselective alkylation to give (6a–c), which were then converted to guanine and hypoxanthine nucleosides, nucleotides, and Acyclovir analogues, respectively.

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