Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of 6, 5'-S- and 6, 5'-N-Cyclouridines (Nucleosides and Nucleotides. XXII)
井上 英夫上田 亨
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キーワード: mass
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1978 年 26 巻 9 号 p. 2664-2667

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抄録
Treatment of 5'-acetylthio-5'-deoxy-2', 3'-O-isopropylidene-5-bromouridine, prepared from 2', 3'-O-isopropylidene-5-bromouridine, with sodium methoxide in methanol afforded 5'-deoxy-5'-thio-2', 3'-O-isopropylidene-S6, 5'-cyclouridine. Deacetonation of the product gave 5'-deoxy-5'-thio-S6, 5'-cyclouridine, a sulfur-bridged cyclouridine fixed in the"anti"conformation. Starting from the 5'-amino derivative a N6, 5'-cyclouridine was similarly prepared. The nuclear magnetic resonance and mass spectra of a series of O-, N- and S-cyclouridines were compared and the characteristic features were discussed.
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© The Pharmaceutical Society of Japan
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