We have synthesized 2'-deoxy-2’ (S)-methylcytidine (7), a new antileukemic nucleoside. The carbonyl methylation of 2’-ketonucleoside (1) with MeLi, Me3Al and MeMgX was examined. Only in the reaction with MeMgX, did the more hindered β -attack afford the 2’-methyl-t-alcohol (2b). Compound 2b was converted into the methyl oxalate (4), which was subjected to radical deoxygenation to give the 2’-deoxy-2’(S)-methyl derivative (_5). The deprotection of 5 followed by substitution with NH3 furnished 7. The structure-activity relationships of 7 and some other 2’-branched-chain sugar cytidines against L1210 cells are also described. © 1987, The Pharmaceutical Society of Japan. All rights reserved.
CITATION STYLE
Matsuda, A., Takenuki, K., Itoh, H., Ueda, T., & Sasaki, T. (1987). Radical Deoxygenation of Tert-Alcohols in 2’-Branched-Chain Sugar Pyrimidine Nucleosides: Synthesis and Antileukemic Activity of 2’-Deoxy-2’(S)-Methylcytidine1). Chemical and Pharmaceutical Bulletin, 35(9), 3967–3970. https://doi.org/10.1248/cpb.35.3967
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