Nucleosides and nucleotide. 145.1synthesis of 2'-deoxy and 5'-phosphate derivatives of bredinin. A photochemical imidazole-ring cleavage and subsequent reconstruction of the base moiety

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Abstract

2'-Deoxy and 5'-phosphate derivatives of bredinin (2 and 3, respectively) were synthesized. UV irradiation of bredinin with a mercury lamp in aqueous HCl gave the imidazole-ring cleavage product 7 in high yield, which was converted to 2'-deoxy derivative 13. Reconstruction of the imidazole ring of 13 with (EtO)3CH and subsequent deprotection afforded the desired 2'-deoxybredinin (2). Similarly, bredinin 5'-phosphate (3) was synthesized via the photo-product 17.

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Shuto, S., Haramuishi, K., & Matsuda, A. (1996). Nucleosides and nucleotide. 145.1synthesis of 2’-deoxy and 5’-phosphate derivatives of bredinin. A photochemical imidazole-ring cleavage and subsequent reconstruction of the base moiety. Tetrahedron Letters, 37(2), 187–190. https://doi.org/10.1016/0040-4039(95)02110-8

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