- Process Development of Tacalcitol
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A highly convergent, gram-scale synthesis of vitamin D3 analogue tacalcitol 1 is disclosed, starting from L-valine and Inhoffen-Lythgoe diol. Key features of the synthesis include modified Julia olefination reaction of β-oxybenzothiazol-2-yl sulfone with C/D ring containing aldehyde to access decagrams of fully functionalized C/D ring synthon. The Horner-Wadsworth-Emmons (HWE) reaction between the C/D ring fragment and commercially available phosphonate completes the carbo-skeleton, which is elaborated into tacalcitol 1 in a gram-scale synthesis.
- Lee, Seung Jong,Moon, Hyung Wook,Lee, Kee-Young,Oh, Chang Young,Kim, U Bin,Shin, Hyunik
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p. 982 - 987
(2021/03/15)
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- Process for Preparing Tacalcitol and Intermediate Therefor
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The present invention relates to a process for preparing tacalcitol and an intermediate body used therefor. According to the preparation method of the present invention, tacalcitol can be effectively and economically prepared without a complex and long preparation process.COPYRIGHT KIPO 2018
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- Enantiomeric impurity PY2 of tacalcitol and preparation method and application thereof
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The invention discloses an enantiomeric impurity PY2 of tacalcitol, i.e., (1 alpha, 3 beta, 5Z, 7E, 24S)-9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol, and a preparation method thereof, and belongsto the technical field of chemical pharmaceutical. The high-purity relevant impurity PY2 of the tacalcitol, which is disclosed by the invention, can be used as an impurity standard substance in the tacalcitol finished product detection analysis so as to promote accurate positioning and nature determination of the tacalcitol finished product detection analysis on the impurity and benefit reinforcement of control on the impurity, thereby improving quality of a tacalcitol finished product. The method provided by the invention has the advantages that the raw materials are cheap and easy to obtain, the operation is simple, the reproducibility is good in and the HPLC (High Performance Liquid Chromatography) purity is greater than or equal to 99.5%.
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- Modified Julia olefination and α aminoxylation reactions mediated convergent synthesis of 1α, 24 (R)-dihydroxyvitamin D3 (tacalcitol)
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A convergent synthesis of tacalcitol has been achieved starting from inexpensive and commercially available isovaleraldehyde and easily available Inhoffen-Lythgoe diol. Key steps include a proline catalyzed α aminoxylation and a Julia-Kocienski olefination.
- Martínez, Andrea,Santalla, Hugo,Garrido, Fátima,Gómez, Generosa,Fall, Yagamare
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p. 3568 - 3570
(2017/10/06)
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- A he cassie is mellow method for the preparation of
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The invention discloses a method for preparing tacalcitol. The method comprises the following steps: with a compound I as a starting raw material, carrying out Wittig reaction, CBS catalytic asymmetric reduction, hydroxy protection, hydrogenation reduction, desilication ether protection and oxidation reaction to prepare a compound VIII, carrying out Wittig Horner reaction on the compound VIII and a known compound IX for coupling, and carrying out dehydroxylation protection to obtain the target compound, namely tacalcitol. With cheap raw materials as the starting point, the method disclosed by the invention is simple, convenient and safe, steps unfavorable to amplification, such as illumination reaction and sodium amalgam reduction reaction, are avoided, and industrial production is facilitated.
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- An efficient stereoselective synthesis of 1α,24(R)-dihydroxyvitamin D3 by the dienyne route
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1α,24(R)-Dihydroxyvitamin D3 (5e) was synthesized. The key step in the preparation of the side-chain was opening of the chiral epoxide 10 by the α-anion of the nitrile 9. The triene system was synthesized by the dienyne route.
- Fall, Yagamare,Torneiro, Mercedes,Castedo, Luis,Mourino, Antonio
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p. 4703 - 4714
(2007/10/03)
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