(1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-{(2-dimethylaminocarbonyl)ethyloxy}preg-na-5-ene

• 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: (1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-{(2-dimethylaminocarbonyl)ethyloxy}preg-na-5-ene
• 英文别名: 3-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17S)-1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethoxy]-N,N-dimethylpropanamide
• 化学式: C₃₈H₇₁NO₄Si₂
• 分子量: 662.157
• InChiKey: ZBHBTBCEYNZKIM-WOMXZONDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.84
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-{(2-dimethylaminocarbonyl)ethyloxy}preg-na-5-ene 在 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 偶氮二异丁腈 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正庚烷 、 甲苯 为溶剂， 反应 105.75h， 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：

  1α,3β-bis<(tert-butyldimethylsilyl)oxy>androst-5-en-17-one 在 15-冠醚-5 、 potassium tert-butylate 、 双氧水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 15.0h， 生成 (1S,3R,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-{(2-dimethylaminocarbonyl)ethyloxy}preg-na-5-ene
  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

• Industrial Synthesis of Maxacalcitol, the Antihyperparathyroidism and Antipsoriatic Vitamin D₃ Analogue Exhibiting Low Calcemic Activity
  作者：Hitoshi Shimizu、Kazuki Shimizu、Noboru Kubodera、Tetsuhiro Mikami、Kaname Tsuzaki、Hiroyuki Suwa、Koji Harada、Akira Hiraide、Motoki Shimizu、Kaichiro Koyama、Yoshihide Ichikawa、Daisuke Hirasawa、Yasushi Kito、Mio Kobayashi、Masaharu Kigawa、Masahiro Kato、Toshiro Kozono、Hideki Tanaka、Makoto Tanabe、Masanori Iguchi、Mitsutaka Yoshida

  DOI：10.1021/op049822x

  日期：2005.5.1

  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.