Selectivity in C-alkylation of dianions of protected 6-methyluridine

Autor: Ngoc Hoa Nguyen, Christophe Len, Anne-Sophie Castanet, Jacques Mortier
Jazyk: angličtina
Rok vydání: 2011
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 7, Iss 1, Pp 1228-1233 (2011)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.7.143
Popis: A regioselective synthesis of 6-ω-alkenyluridines 3, precursors of potent antiviral and antitumor cyclonucleosides 5, is described. While ω-alkenyl halides do not alkylate 6-lithiouridine, compounds 3 were prepared in a regioselective manner by sequential treatment of 6-methyluridine 2 with LTMP or LDA (4 equiv) in THF at −30 °C followed by alkylation with ω-alkenyl bromides.
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