Facile methods for the synthesis of 5-formylcytidine

5'-O-Protected 5-methylcytidine 3 was oxidized with Na2S2O8 to give a mixture of the corresponding 5-(hydroxymethyl)- and 5-formylcytidine derivatives, 4 and 5. The hydroxymethyl group of 4 was further oxidized to a formyl group by treatment with ceric(IV) ammonium nitrate (CAN). Alternatively,...

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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 6; pp. 1061 - 1063
Main Authors Rahman, AAHA, Wada, T, Saigo, K
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 05.02.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
NUCLEOSIDES
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Summary:5'-O-Protected 5-methylcytidine 3 was oxidized with Na2S2O8 to give a mixture of the corresponding 5-(hydroxymethyl)- and 5-formylcytidine derivatives, 4 and 5. The hydroxymethyl group of 4 was further oxidized to a formyl group by treatment with ceric(IV) ammonium nitrate (CAN). Alternatively, 2',3',5'-0-protected 5-(hydroxymethyl)cytidine 10 was directly oxidized with CAN to give the desired 5-formylcytidine derivative 11. After removal of the protecting groups in each intermediate, 5-formylcytidine (6) was obtained in good yield. (C) 2001 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/s0040-4039(00)02191-2