Synthesis of 6,2'-Methano-cyclouridine, a Uridine Fixed in High-Anti Conformation (Nucleosides and Nucleotides. LX)
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概要
- 論文の詳細を見る
The reaction of methylenetriphenylphosphorane with 2'-keto-3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl) uridine afforded the 2'-methyleneuridine (1). Oxidation of 1 with osmium tetroxide and tert-butyl hydroperoxide or N-methylmorpholine-N-oxide afforded a mixture of a 2'-hydroxymethyluridine (2) and its arabinosyl isomer. Oxidation at lower temperature gave the former as the main product. Compound 2 was converted to the 5-bromo-2'-iodomethyl derivative (3) through the 2'-mesyloxy compound, and 3 was treated with tri-n-butyltin hydride to give the 6,2'-methano-cyclo-5,6-dihydro derivative (4). Compound 4 was dehydrobrominated and deprotected to furnish 6,2'-methano-cyclouridine, a uridine fixed in high-anti conformation. Some results on the synthesis and cleavage of the 2'-spiro-epoxy derivative prepared from the 2'-ketouridine are also presented.
- 社団法人日本薬学会の論文
- 1985-09-25
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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周東 智
Research Laboratories Toyo Jozo Co. Ltd
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佐野 友春
Faculty of Pharmaceutical Sciences, Hokkaido University
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周東 智
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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佐野 友春
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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井上 英夫
Faculty Of Pharmaceutical Sciences Hokkaido University
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