Synthesis of 5-substituted 2'-deoxyuridines

…, CJ Pillar, WJ Woodford, MP Mertes

Index: Kampf; Pillar; Woodford; Mertes Journal of Medicinal Chemistry, 1976 , vol. 19, # 7 p. 909 - 915

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Citation Number: 26

Abstract

Another approach to a derivative of the formyl 9 that would be more stable under phosphorylation conditions is through the dithiolane analogue. Treatment of the protected formyl nucleoside 6 with ethanedithiol in a BF3-catalyzed reaction gave an 84% yield of 10. Basecatalyzed transesterification converted 10 to the nucleoside 11. The ultraviolet maxima of 11 at 270 nm is midway between the maxima for a 5-substituted CH3 or CHzOR ...