Acetic Acid → 2',3'-Didehydro-2',3'-dideoxycytidine

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Reaction Steps

Namely, 2',3'-dideoxycytidine can be obtained according to the method of Horwitz et al in a way that N-benzoyl-2'-deoxy-3',5'-di-0-mesylcytidine derivable from 2'-deoxycytidine is refluxed with aqueous solution of sodium hydroxide in ethanol, then this is treated with dilute acetic acid, and further allowed to react with potassium tert-butoxide in dimethyl sulfoxide to obtain 2',3'-dideoxy-2',3'-didehydrocytidine, which is hydrogenated (J. Org. Chem., 32, 817, 1967).

Provenance & Evidence