Synthesis of C-Nucleosides via [2+4] Cycloaddition of Ketene Intermediate
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概要
- 論文の詳細を見る
Reaction of 2,3,5-tri-O-benzyl-D-ribofuranose (4) with carboalkoxychloromethylenetriphenyl-phosphoranes (5a, b) gave an E, Z mixture of the corresponding alkyl 4,5,7-tri-O-benzyl-2-chloro-2,3-dideoxy-D-ribo-hept-2-enonates (6a, b). Cyclization of 6a, b with triethylamine afforded exclusively the β-C-glycosides 7a, b which were diastereomeric at the carbon bearing chlorine. Hydrolysis of 7a, b with 5% aq. sodium hydroxide in dioxane gave the carboxylic acid 8. Treatment of 8 with thionyl chloride (or trifluoroacetic anhydride) in the presence of triethylamine, followed by reaction with the 2-arylideneaminopyridine 2a or ethyl N-(2-pyridyl) formimidates (2b, c) gave the corresponding fully protected pyrido [1,2-a] pyrimidine C-nucleosides (15a-c), which were deprotected with boron trichloride to give the C-nucleosides (17b, c).
- 公益社団法人日本薬学会の論文
- 1985-07-25
著者
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加藤 鐵三
Central Research Institute Mect Corporation
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加藤 鐵三
Pharmaceutical Institute. Tohoku University
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片桐 信弥
Pharmaceutical Institute, Tohoku University
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羽田 融
Pharmaceutical Institute, Tohoku University
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丹羽 龍史
Central Research Institute Mect Corporation
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片桐 信弥
Health Sci. Univ. Hokkaido Hokkaido Jpn
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片桐 信弥
Pharmaceutical Institute Tohoku University
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丹羽 龍史
Pharmaceutical Institute, Tohoku University
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羽田 融
Pharmaceutical Institute Tohoku University
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