- Industrial synthesis of maxacalcitol, the antihyperparathyroidism and antipsoriatic vitamin D3 analogue exhibiting low calcemic activity
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Maxacalcitol, the 22-oxa-derivative of 1α,25-dihydroxyvitamin D 3 and used currently as an antihyperparathyroidism and antipsoriatic drug, has been synthesized in seven chemical steps from 1α- hydroxydehydroepiandrosterone on the basis of our previously developed route. The present synthesis allows the production of the protected form of the penultimate intermediate in 26% overall yield in a kilogram scale reaction employing neither difficult reaction conditions nor chromatographic purification, having overcome all the difficulties involved in the previous route.
- Shimizu, Hitoshi,Shimizu, Kazuki,Kubodera, Noboru,Mikami, Tetsuhiro,Tsuzaki, Kaname,Suwa, Hiroyuki,Harada, Koji,Hiraide, Akira,Shimizu, Motoki,Koyama, Kaichiro,Ichikawa, Yoshihide,Hirasawa, Daisuke,Kito, Yasushi,Kobayashi, Mio,Kigawa, Masaharu,Kato, Masahiro,Kozono, Toshiro,Tanaka, Hideki,Tanabe, Makoto,Iguchi, Masanori,Yoshida, Mitsutaka
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p. 278 - 287
(2012/12/24)
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- An alternative and efficient synthesis of 24,24-difluoro-1α,25-dihydroxyvitamin D3
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An alternative synthesis of the title compound 2, a highly potent analog of 1α,25-dihydroxyvitamin D3 (1), is described. Starting with 1α,3β-bis[(tert-butyldimethylsilyl)oxy]androst-5-ene (8), 2 was obtained in 3.8% total yield through 10 steps. This method provides compound 2 in much higher yield than that reported previously.
- Konno,Ojima,Hayashi,Takayama
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p. 1120 - 1124
(2007/10/02)
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- Process for the preparation of 24,24-difluoro-1α,25-dihydroxy vitamin D3 and intermediates obtained therefrom
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The present invention relates to a process and intermediates for the preparation of 24,24-difluoro-1α,25-dihydroxycholecalciferol from the readily-available 1α,3β-dihydroxyandrost-5-en-17-one which is made by a known microbiological process from 3β-hydroxyandrost-5-en-17-one [R. M. Dodson, A. H. Goldkamp and R. D. Muir, J. Amer. Chem. Soc. 82 4026 (1960)].
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