(17Z)-(1S,3R)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5, 17-dien | 143101-51-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (17Z)-(1S,3R)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5, 17-dien
• 英文别名: (17Z)-(1S,3R)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5,17-diene；tert-butyl-[[(1S,3R,8S,9S,10R,13S,14S,17Z)-1-[tert-butyl(dimethyl)silyl]oxy-17-ethylidene-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-dimethylsilane
• CAS: 143101-51-3
• 化学式: C₃₃H₆₀O₂Si₂
• 分子量: 545.009
• InChiKey: LGSSQVJCUVOLNM-FMHXBDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.29
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (17Z)-(1S,3R)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5, 17-dien 在 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 四丁基氟化铵 、 双氧水 、 L-Selectride 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正庚烷 、 甲苯 、 mineral oil 为溶剂， 反应 110.75h， 生成 马沙骨化醇
  参考文献：
  名称：

  Industrial Synthesis of Maxacalcitol, the Antihyperparathyroidism and Antipsoriatic Vitamin D₃ Analogue Exhibiting Low Calcemic Activity

  摘要：

  Maxacalcitol, the 22-oxa-derivative of 1 alpha,25-dihydroxyvitamin D-3 and used currently as an antihyperparathyroidism and antipsoriatic drug, has been synthesized in seven chemical steps from 1 alpha-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.

  DOI：

  10.1021/op049822x
• 作为产物：
  描述：

  1-羟基去氢表雄酮 在 咪唑 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (17Z)-(1S,3R)-1,3-bis(tert-butyldimethylsilyloxy)pregna-5, 17-dien
  参考文献：
  名称：

  Industrial Synthesis of Maxacalcitol, the Antihyperparathyroidism and Antipsoriatic Vitamin D₃ Analogue Exhibiting Low Calcemic Activity

  摘要：

  Maxacalcitol, the 22-oxa-derivative of 1 alpha,25-dihydroxyvitamin D-3 and used currently as an antihyperparathyroidism and antipsoriatic drug, has been synthesized in seven chemical steps from 1 alpha-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.

  DOI：

  10.1021/op049822x

文献信息

• PROCESS FOR PRODUCING VITAMIN D DERIVATIVE USING PHOTOREACTION
  申请人：Kawase Akira

  公开号：US20100261917A1

  公开（公告）日：2010-10-14

  There are provided a novel process for producing [(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-9,10-secopregna-5,7,10(19),16-tetraen-20-yl}oxy]-N-(2,2,3,3,3-pentafluoropropyl)acetamide, which process is characterized by irradiating a compound represented by the formula: with UV to ring-open the compound, and then isomerizing the resulting compound; an intermediate useful for carrying out the process; and a process for producing the intermediate.

  提供了一种新的生产[(5Z,7E)-(1S,3R,20S)-1,3-二羟基-9,10-分裂孕酮-5,7,10(19),16-四烯-20-基}氧]-N-(2,2,3,3,3-五氟丙基)乙酰胺的方法，其特征在于用紫外线照射代表以下公式的化合物使其环开裂，然后异构化所得化合物；用于执行该过程的中间体；以及生产该中间体的方法。
• METHOD FOR PRODUCING VITAMIN D DERIVATIVE UTILIZING PHOTOREACTION
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1961740B1

  公开（公告）日：2013-04-24
• Design and evaluation of new antipsoriatic antedrug candidates having 16-en-22-oxa-vitamin D3 structures
  作者：Kazuki Shimizu、Akira Kawase、Tsuyoshi Haneishi、Yasuharu Kato、Kazutomo Kinoshita、Masayuki Ohmori、Yoshiyuki Furuta、Takashi Emura、Nobuaki Kato、Tetsuya Mitsui、Koji Yamaguchi、Keiichi Morita、Nobuo Sekiguchi、Tessai Yamamoto、Tomochika Matsushita、Shin Shimaoka、Atsuko Sugita、Kazumi Morikawa

  DOI：10.1016/j.bmcl.2006.03.014

  日期：2006.6

  Design, synthesis, and in vitro and in vivo evaluation of a series of antipsoriatic antedrugs having 16-en-22-oxa-vitamin D-3 are described. Among the seven compounds examined, two are promising: ester 5c and amide 5f, both of which exhibit greater potent antiproliferation activity with lessened calcemic activity than the presently prescribed maxacalcitol (2). (c) 2006 Elsevier Ltd. All rights reserved.
• Org. Process Res. Dev. 2005, 9, 278-287
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  日期：——
• Bioorg. Med. Chem. Lett. 2006, 16, 3323-3329
  作者：

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  日期：——