期刊
TETRAHEDRON
卷 67, 期 10, 页码 1915-1923出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.01.020
关键词
Pseudouridine; Nitrones; Pyrrolidines; Dipolar cycloaddition; Modified nucleosides
Pyrrolidine analogues of C-nucleosides related to pseudouridine have been synthesized by 1,3-dipolar cycloaddition reactions of uracil-5 and 2,4-dimethoxypyrimidine-5 nitrones with allyl alcohol and methyl acrylate, and subsequent reductive cleavage of the isoxazolidine cycloadducts. The dimethoxy derivatives have been easily deprotected to the corresponding uracils bearing the pyrrolidine ring instead of a sugar moiety. The regio and stereoselectivity of the reactions are discussed. (C) 2011 Elsevier Ltd. All rights reserved.
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