Summary
N2-Substituted 5-methylisocytidine derivatives were synthesized from S2-methyl-2-thiothymine either by direct substitution of the methylthio group by an amino group and subsequent condensation with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose to give the acetylated nucleoside or by the opposite sequence first preparing an acetylated 5,S2-dimethyl-2-thiouridine followed by treatment with the appropriate amine.
Zusammenfassung
N2-substituierte 5-Methylisocytidin-Derivate wurden ausgehend von S2-Methyl-2-thiothymidin entweder durch direkte Substitution der Methylthiogruppe durch eine Aminogruppe und anschließende Kondensation mit 1,2,3,5-tetra-O-Acetyl-β-D-ribofuranose zum acetylierten Nucleosid oder umgekehrt durch Synthese eines acetylierten 5,S2-Dimethyl-2-thiouridins und nachfolgende Behandlung mit dem entsprechenden Amin hergestellt.
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References
Piccirilli JA, Krauch T, Moroney SE, Benner SA (1990) Nature (London)343: 33
Tor Y, Dervan PB (1993) J Am Chem Soc115: 4461
Switzer CY, Moroney SE, Benner SA (1993) Biochemistry32: 10489
Strobel SA, Cech TR, Usman N, Beigelman L (1994) Biochemistry33: 13824
Skaric V, Gaspert B, Hohnjec M, Lancan G (1974) J Chem Soc Perkin Trans1, 267
Minamoto K, Azuma K, Tamaka T, Iwasaki I, Eguchi S, Kadaya S, Moroi R (1988) J Chem Soc Perkin Trans1, 2955
Vorbrüggen H, Krolikiewicz K, Bennua B (1981) Chem Ber114: 1234
Niedballa U, Vorbrüggen H (1974) J Org Chem39: 3654
Abdel-Rahman AA-H, Zahran MA, Abdel-Megied AE-S, Pedersen EB, Nielsen C, Synthesis (in press)
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Abdel-Rahman, A.A.H., Pedersen, E.B. & Nielsen, C. Synthesis of 5-methylisocytidine derivatives. Monatsh Chem 127, 455–459 (1996). https://doi.org/10.1007/BF00810888
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DOI: https://doi.org/10.1007/BF00810888