3β-[(1-hydroxycyclohexyl)methyl]-5α-cholestan-3α-ol

• 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: 3β-[(1-hydroxycyclohexyl)methyl]-5α-cholestan-3α-ol
• 英文别名: (3R,5S,8R,9S,10S,13R,14S,17R)-3-[(1-hydroxycyclohexyl)methyl]-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-ol
• 化学式: C₃₄H₆₀O₂
• 分子量: 500.849
• InChiKey: AJMZEYAEBISNKM-SRWBXIRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 4,4'-二叔丁基苯并 、 potassium tert-butylate 、 lithium 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 5.67h， 生成 3β-[(1-hydroxycyclohexyl)methyl]-5α-cholestan-3α-ol
  参考文献：
  名称：

  Synthesis of functionalised enantiopure steroids from estrone and cholestanone through organolithium intermediates

  摘要：

  The reaction of epoxides I and 8 derived from estrone and cholestanone, respectively. with an excess of lithium and a catalytic amount of DTBB (7 mol%) in THF at -78 degreesC led to formation of the correlsponding beta -oxido-functionalised organolithium intermediates 2 and 9, respectively, in a regio- and stereoselective manner. Treatment of these intermediates with different electrophiles [H2O, D2O, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, CO2] at -78 to 20 degreesC afforded, after hydrolysis with water. enantiomerically purr derivatives 3 and 10. respectively. When protected ketones 5 and 6 derived from D-glucose and D-fructose were used as the electrophile. the reaction with 2 gave the expected mixed products 3g and 3h, respectively. which consist of a steroid and a carbohydrate fragment. The fraction of O-protected estrone 4 as the electrophilic component and intermediate 2 afforded the C-2-symmetric steroid dimer 3f. The stereochemistry of the products was unambiguously determined by correlation with X-ray data for compound 3d and by comparison with the known compound 6a. Finally. thr addition of the dianions 13, resulting from the DTBB-catalysed lithiation of phthalan 12a and isochroman 12b, to the O-protected estrone 4 and to cholestanone 9 led to the Formation of the diols 14, 15 and 16. Diols 14 were cyclised under Mitsunobu reaction conditions to the corresponding heterocycles 17. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00121-5

文献信息

• Structural modification of steroids through functionalised organolithium compounds
  作者：Larry R Falvello、Francisco Foubelo、Tatiana Soler、Miguel Yus

  DOI：10.1016/s0957-4166(00)00175-0

  日期：2000.6

  The reaction of the epoxysteroids 1 and 4, derived from estrone and cholestanone, respectively, with an excess of lithium and a catalytic amount of DTBB (7 mol%) in THF at -78 degrees C, leads to the formation of the corresponding P-oxido-functionalised organolithium intermediates 2 and 5, respectively, which, by reaction with different electrophiles [H2O, D2O, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, CO2] at -78 degrees C to room temperature, afford, after hydrolysis with water? enantiomerically pure compounds 3 and 6, respectively. The stereochemistry of all these compounds was unambiguously determined by correlation with X-ray data for compound 3d and by comparison with the known compound 6a. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of functionalised enantiopure steroids from estrone and cholestanone through organolithium intermediates
  作者：Miguel Yus、Tatiana Soler、Francisco Foubelo

  DOI：10.1016/s0957-4166(01)00121-5

  日期：2001.4

  The reaction of epoxides I and 8 derived from estrone and cholestanone, respectively. with an excess of lithium and a catalytic amount of DTBB (7 mol%) in THF at -78 degreesC led to formation of the correlsponding beta -oxido-functionalised organolithium intermediates 2 and 9, respectively, in a regio- and stereoselective manner. Treatment of these intermediates with different electrophiles [H2O, D2O, PhCHO, Me2CO, Et2CO, (CH2)(5)CO, CO2] at -78 to 20 degreesC afforded, after hydrolysis with water. enantiomerically purr derivatives 3 and 10. respectively. When protected ketones 5 and 6 derived from D-glucose and D-fructose were used as the electrophile. the reaction with 2 gave the expected mixed products 3g and 3h, respectively. which consist of a steroid and a carbohydrate fragment. The fraction of O-protected estrone 4 as the electrophilic component and intermediate 2 afforded the C-2-symmetric steroid dimer 3f. The stereochemistry of the products was unambiguously determined by correlation with X-ray data for compound 3d and by comparison with the known compound 6a. Finally. thr addition of the dianions 13, resulting from the DTBB-catalysed lithiation of phthalan 12a and isochroman 12b, to the O-protected estrone 4 and to cholestanone 9 led to the Formation of the diols 14, 15 and 16. Diols 14 were cyclised under Mitsunobu reaction conditions to the corresponding heterocycles 17. (C) 2001 Elsevier Science Ltd. All rights reserved.