Reaction of 5-Bromouridine Derivatives with Dimethyl Malonate Carbanion. A Novel Entry to the Synthesis of Uridine-5-acetic Acids
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概要
- 論文の詳細を見る
The reaction of N^3,5'-O-dibenzoyl-2', 3'-O-isopropylidene-5-bromouridine (1) with dimethyl malonate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene afforded a 5-malonate ester derivative (2) in high yield. Uridine-5-acetic acid (7) and its methyl ester (4), minor nucleosides in transfer ribonucleic acids, could be readily obtained from 2 via removals of one carboxyl function and protecting groups. Treatment of N^3,5'-O-dibenzoyl-2', 3'-O-isopropylideneuridine (8) with the carbanion of ethyl acetoacetate caused degradation of the base moiety to give an N^3-benzoyl-ribosylurea derivative (9) in good yield. Possible mechanisms of these reactions are proposed.
- 社団法人日本薬学会の論文
- 1986-11-25
著者
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上田 亨
Faculty of Pharmaceutical Science, Hokkaido University
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上田 亨
Faculty Of Pharmaceutical Sciences Hokkaido University
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井上 英夫
Faculty of Pharmaceutical Sciences, Hokkaido University
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井上 英夫
北海道大学薬学部
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斎藤 直美
Faculty of Pharmaceutical Sciences, Hokkaido University
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上田 亨
北海道大学薬学部
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斎藤 直美
Faculty Of Pharmaceutical Sciences Hokkaido University
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井上 英夫
Faculty Of Pharmaceutical Sciences Hokkaido University
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