Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Diethylaminosulfur Trilfluoride (DAST) as a Fluorinating Agent of Pyrimidine Nucleosides Having a 2', 3'-Vicinal Diol System
早川 弘之高井 富美田中 博道宮坂 貞山口 健太郎
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1990 年 38 巻 5 号 p. 1136-1139

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Displacement of a hydroxyl group in pyrimidine nucleosides having a vicinal diol system by a fluorine atom was investigated by using diethylaminosulfur trifluoride (DAST). Though participation of the base moiety often thwarts the desired introduction of a fluorine atom, it was found that appropriate modification of the base and/or sugar moieties allowed the desired fluorodehydroxylation to occur, giving 5'-, 3'-β-, and 2'-α-fluorinated uracilnucleosides in good yields.

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