- Improved and efficient synthesis of Maxacalcitol
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Maxacalcitol, the 22-oxa-derivative of 1α, 25-dihydroxyvitamin D 3, has been used as an antihyperparathyroidism and antipsoriatic drug. In this paper, an alternative synthetic route has been developed using commercially available vitamin D
- Feng, Shi,Cui, Li-Fei,Wei, He-Geng,Zheng, Guo-Jun,Wang, Ya-Ping,Wang, Xiang-Jing,Zhang, Ji,Xiang, Wen-Sheng
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- Synthesis of tritiated 1α,25-dihydroxy-22-oxavitamin D3
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Synthesis of two tritiated 1α,25-dihydloxy-22-oxavitamin D3 (OCT), [26-3H3]OCT (3) and [2β-3H]OCT (4), is described. [26-3H3]OCT (3) was prepared by tritiation at the side chain with tritia
- Watanabe,Akiyama,Kawanishi,Kubodera
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- Stereoselective synthesis of 22-oxacalcitriol (OCT) and analogues modified at C25
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The stereoselective synthesis of 22-oxacalcitriol (OCT) has been achieved. The triene system was introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach to couple ketoester 7 with A ring phosphine oxide 8. The value of the resulting ester 6 for synthesis of C25-modified OCT analogues is exemplified by the synthesis of 5.
- Fall, Yagamare,González, Victoria,Vidal, Beatriz,Mouri?o, Antonio
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- A MARTHA calciferol preparation method (by machine translation)
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The invention belongs to the field of pharmaceutical chemistry, and in particular relates to a preparation method of MARTHA calciferol. The method as the compound 1 as the starting material, through the tosylates selective protection secondary hydroxy, under the action of alkali, in methanol occurs in the intramolecular cyclization reaction to produce the compound 3, 3 through the alkene third oxidation, selective protection secondary hydroxy to obtain compound 5, compound 5 in opened under the effect of triatomic acid to obtain compound 6, compound 6 deprotected base to obtain the target compound. The invention raw materials are easy, simple operation, the step is short, only 6 step reaction. (by machine translation)
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- SYNTHETIC INTERMEDIATE OF MAXACALCITOL, PREPARATION METHOD THEREFOR AND USE THEREOF
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The present invention provides a new method for synthesizing maxacalcitol and an intermediate thereof. According to the method, the maxacalcitol is creatively synthesized through the steps of: taking vitamin D2 as an initial raw material, obtaining a compound represented by formula II, oxidizing, chirally reducing, grafting with a side chain, introducing a hydroxyl group on the C-1 position, and photochemically overturning.
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Paragraph 0121; 0122; 0123; 0124
(2016/09/26)
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- 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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- Ultraviolet irradiation apparatus for photochemical reaction and preparation process of vitamin D derivative making use of the same
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Disclosed herein are an ultraviolet irradiation apparatus for photochemical reactions which can irradiate the photo-reactive solution with ultraviolet rays having a specific wavelength suitable for the intended photochemical reaction at a high efficiency, and a process by which a provitamin D derivative can be converted into a provitamin D derivative at a high efficiency by means of a photochemical reaction by one-step process of light irradiation, thereby preparing a vitamin D derivative at a high efficiency. The ultraviolet irradiation apparatus irradiates the photo-reactive solution with the ultraviolet rays having the specific wavelength through a quartz rod. Specifically, the apparatus is constructed by an electric discharge lamp, a condensing and reflecting mirror and a plane mirror both having wavelength selective property, an optical filter which transmits the ultraviolet rays having the specific wavelength, and a quartz rod on which the ultraviolet rays having the specific wavelength are struck. The photo-reactive solution is irradiated with the ultraviolet rays from the quartz rod. The quartz rod is immersed in the photo-reactive solution, or a reaction vessel is irradiated with the ultraviolet rays from the quartz rod. In the preparation process of the vitamin D derivative, an ultraviolet irradiation apparatus for photochemical reactions having an ultraviolet radiation-emitting lamp, an optical system having wavelength selective property and a quartz rod on which the ultraviolet rays having the specific wavelength from the optical system are struck is used, and a solution of a provitamin D derivative is irradiated with the ultraviolet rays having the specific wavelength emitted from the quartz rod to cause a photochemical reaction of the provitamin D derivative solution, thereby forming a previtamin D derivative. The previtamin D derivative is further subjected to a thermal isomerization reaction to prepare the vitamin D derivative.
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- Synthetic studies of vitamin D analogues. XI. Synthesis and differentiation-inducing activity of 1α-25-dihydroxy-22-oxavitamin D3 analogues
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Six analogues of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 26,27-dimethyl OCT (5), 26,27-diethyl OCT (6), 24-norOCT (7), 24-homoOCT (8), 24-dihomoOCT (9), and 24-trihomoOCT (10) were synthesized from the 20(S)-alcohol (11) as the common start
- Kubodera,Watanabe,Kawanishi,Matsumoto
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p. 1494 - 1499
(2007/10/02)
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