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Communication | Special issue | Vol 42, No. 1, 1996, pp.149-154
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S57
Nucleosides and Nucleotides. 138. Synthesis of 3-Halo-3-deazainosines: Conformational Lock with the Halogen at the 3-Position of the 3-Deazainosine in anti-Conformation

Noriaki Minakawa, Naoshi Kojima, and Akira Matsuda

*Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

Abstract

Synthesis of 3-chloro-, bromo-, and iodo-3-deazainosines (6-8) can be done by treatment of the 3-deazainosine derivative (2) with N-halosuccinimides. Treatment of the 5-formylimidazole derivative (11) with vinylmagnesium bromide gave 5-(1-hydroxy-2-propenyl)imidazole derivative (12), followed by fluorination and appropriate manipulations to cyclize, affording 3-fluoro-3-deazainosine (18). Although free rotation around the glycosyl linkage in 3-deazainosine (1) and 18 was observed, those of 6, 7, and 8 were rather fixed in the anti-conformation as analyzed by nOe experiments.