Nucleosides-126. Selective methylation of the C-nucleoside, ψ-isocytidine and its 2 $ ́-deoxy analog. Synthesis of 1-methyl, 3-methyl and 4-o-methyl derivatives

K. W. Pankiewicz, A. Matsuda, K. A. Watanabe, J. J. Fox

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Abstract

Methods were developed to prepare 1 -methyl-, 3-methyl- and 4-0-methyl-ψ-isocytidine by selective methylation.3, ́5 - ́O-Tetraisopropyldisiloxanyl-ψ isocytidine (8) was trimethylsilylated and then treated with MeI and, after deprotection, 1 -methyl-ψ isocytidine (6) was obtained. The 2 - ́deoxy analog (7) was also prepared in a similar manner from the 2 - ́deoxy analog (10) of 8. Treatment of 8 with CH2N2 afforded the 3-methyl-ψ-isocytidine derivative (19) as the major product. Methylation with diazomethane also occurred mainly on N3 of the 2 - ́deoxy analog 10 to form 20. Removal of the 3, ́ 5 - ́O-protecting group from 19 and 20 afforded 3-methyl-ψ-isocytidine (14) and its 2-deoxy analog (15), respectively. 2-N-Acetyl- 3, ́5 - ́O-tetraisopropyldisiloxanyl-ψ-isocytidine (24), on the other hand, gave the 4-O-methyl derivative (25) as the major product upon CH2N2 treatment. Subsequent deprotection of 25 afforded 4-O-methyl-ψ-isocytidine (29). aiv51b1p33b.

Original languageEnglish (US)
Pages (from-to)33-38
Number of pages6
JournalTetrahedron
Volume40
Issue number1
DOIs
StatePublished - 1984

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