- Efficient synthesis of 5-hydroxymethyl pyrimidines and their nucleosides using microwave irradiation
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Hydroxymethylation of uracil (1), cytosine (3), 5-hydroxymethyl-2′,3′-O-isopropylideneuridine (5), 5′-O-tert-butyldiphenylsilyl-2′,3′-O-isopropylideneuridine (7), 2′,3′-O-isopropylidenecytidine (9) and 2′,3′-O-isopropylidene-5′-O-tritylcytidine (11) was efficiently carried out with paraformaldehyde in alkaline medium under microwave irradiation in very high yield.
- Abdel-Rahman, Adel A.-H.,El Ashry, El Sayed H.
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p. 2043 - 2044
(2007/10/03)
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- Facile methods for the synthesis of 5-formylcytidine
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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′-O-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.
- Abdel Rahman, Adel A.-H.,Wada, Takeshi,Saigo, Kazuhiko
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p. 1061 - 1063
(2007/10/03)
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