著者

林 貴昭 尾島 克二 紺野 勝弘 間中 明彦 山口 健太郎 山田 幸子 高山 浩明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.40, no.11, pp.2932-2936, 1992-11-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

5 4

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A new synthesis of 24-fluoro-1α, 25-dihydroxyvitamin D2 (4a) and its 24-epimer (4b) is described. Starting with 1α, 3β-bis[(tert-butyldimethylsilyl)oxy]-24-norchol-5, 7-dien-23-al (5), a mixture of 4a and 4b was obtained in 3% overall yield in 6 steps. Reversed-phase HPLC cleanly separated the mixture into the two C-24 epimers. The X-ray crystallographic analysis of the 4-phenyl-1, 2, 4-triazoline-3, 5-dione (PTAD) adduct 11b, which was derived from the ester 6, unambiguously determined the configuration at C-24 of this compound. Based on the X-ray analysis, the configuration at C-24 of 4a and 4b was unequivocally determined.