(8S,20R)-des-A,B-20-(1',1'-dimethyl-3'-ethoxycarbonyl-propyl)pregnan-8β-ol | 1335097-67-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (8S,20R)-des-A,B-20-(1',1'-dimethyl-3'-ethoxycarbonyl-propyl)pregnan-8β-ol
• 英文别名: (8S,20R)-des-A,B-20-(1'-dimethyl-3'-ethyloxycarbonyl-propyl)pregnan-8-ol；ethyl (5R)-5-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-4,4-dimethylhexanoate
• CAS: 1335097-67-0
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: LRVFEOPYJOHPBE-GFAJBQDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,20R)-des-A,B-20-(1',1'-dimethyl-3'-ethoxycarbonyl-propyl)pregnan-8β-ol 在 2,6-二甲基吡啶 、 四丙基高钌酸铵 、 苯基锂 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 di-n-buthyl ether 为溶剂， 反应 44.5h， 生成 (20R)-1α-[(tert-butyldimethylsilyl)oxy]-22,22-dimethyl-25-[(triethylsilyl)oxy]-2-methylene-19-norvitamin D(3) tert-butyldimethylsilyl ether
  参考文献：
  名称：

  (20S)-2-METHYLENE-19-NOR-22-DIMETHYL-1alpha,25-DIHYDROXYVITAMIN D3 AND (20R)-2-METHYLENE-19-NOR-22-DIMETHYL-1alpha,25-HYDROXYVITAMIN D3

  摘要：

  提供了具有公式I的化合物，其中X1、X2和X3分别选择自H或羟基保护基团。这些化合物可用于制备药物组合物，并可用于治疗各种生物条件。

  公开号：

  US20110237556A1
• 作为产物：
  描述：

  (8S,20R)-des-A,B-20-(1',1'-dimethyl-3'-ethoxycarbonyl-allyl)-8β-[(triethylsilyl)oxy]pregnane 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以68%的产率得到(8S,20R)-des-A,B-20-(1',1'-dimethyl-3'-ethoxycarbonyl-propyl)pregnan-8β-ol
  参考文献：
  名称：

  (20S)-2-METHYLENE-19-NOR-22-DIMETHYL-1alpha,25-DIHYDROXYVITAMIN D3 AND (20R)-2-METHYLENE-19-NOR-22-DIMETHYL-1alpha,25-HYDROXYVITAMIN D3

  摘要：

  提供了具有公式I的化合物，其中X1、X2和X3分别选择自H或羟基保护基团。这些化合物可用于制备药物组合物，并可用于治疗各种生物条件。

  公开号：

  US20110237556A1

文献信息

• A 20<i>S</i> Combined with a 22<i>R</i> Configuration Markedly Increases both in Vivo and in Vitro Biological Activity of 1α,25-Dihydroxy-22-methyl-2-methylene-19-norvitamin D₃
  作者：Agnieszka Flores、Rafal R. Sicinski、Pawel Grzywacz、James B. Thoden、Lori A. Plum、Margaret Clagett-Dame、Hector F. DeLuca

  DOI：10.1021/jm300187x

  日期：2012.5.10

  Six new analogues of 1 alpha,25-dihydroxy-19-norvitamin D-3 (3a-4b, 5, and 6) were prepared by a convergent synthesis applying the Wittig-Horner reaction as a key step. The influence of methyl groups at C-22 on their biological activity was examined. It was established that both in vitro and in vivo activity is strongly dependent on the configuration of the stereogenic centers at C-20 and C-22. Introduction of the second methyl group at C-22 (analogues 5 and 6) generates the compounds that are slightly more potent than 1 alpha,25-(OH)(2)D-3 in the in vitro tests but much less potent in vivo. The greatest in vitro and in vivo biological activity was achieved when the C-20 is in the S configuration and the C-22 is in the R configuration. The building blocks for the synthesis, the respective (20R,22R)-, (20R,22S)-, (20S,22R)-, and (20S,22S)-diols, were obtained by fractional crystallization of mixtures of the corresponding diastereomers. Structures and absolute configurations of the diols 21a, 21b, and 22a as well as analogues 3a, 5, and 6 were confirmed by the X-ray crystallography.