著者

木村 純二 平 潔 後藤 伸治 泉水 裕二

出版者

公益社団法人 日本化学会

雑誌

日本化学会誌(化学と工業化学) (ISSN:03694577)

巻号頁・発行日

vol.1988, no.7, pp.1122-1123, 1988-07-10 (Released:2011-05-30)

参考文献数

12

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Conformational analyses of 2′, 3′-O-methylene- [1], 2′, 3′-O-isopropylidene- [2], 2′, 3′-O-isobutylmethylene- [3], 2′, 3′-O-diheptylmethylene- [4], and 2′, 3′-O-diphenylmethyleneuridine [5] are examined by interpretation of proton magnetic resonance coupling constants and quantitative application of the nuclear overhauser effect (NOE). Dihedral anglesφ 1′, 2′ and φ 3′, 4′ in DMSO-d6 at 22±1°C are slightly broadened in the order [1]>[2]>[3]≅[4]≅[5] because of the effect of steric barrier of alkylidene group. Under the same conditions, these compounds are found to exist primary in the syn-like conformation from NOE measurement. It is clarified that the population of the anti-conformation such as 2, 2′- and 2, 3′-anhydro nucleosides increases ([4]>[5]≅[3]>[2]>[1]) with the increase of bulkiness of the substituent of 2′, 3′-O-alkylidene group.