(S)-4-[(3R,8R,9R,10S,13S,14R,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanal | 548459-80-9

• 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: (S)-4-[(3R,8R,9R,10S,13S,14R,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanal
• CAS: 548459-80-9
• 化学式: C₃₀H₅₂O₂Si
• 分子量: 472.827
• InChiKey: SJKYBZKXRMDCDB-YRQGZSEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.57
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-4-[(3R,8R,9R,10S,13S,14R,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanal 在 platinum on activated charcoal 正丁基锂 、 四丁基氟化铵 、 氘 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 ent-deuterocholesterol
  参考文献：
  名称：

  First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

  摘要：

  We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00174-5
• 作为产物：
  描述：

  dl-Δ⁴-androstene-3,17-dione 在 platinum on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 chromium trioxide-pyridine complex 、 Celite 、 potassium tert-butylate 、 氢气 、 sodium acetate 、 氯化二乙基铝 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， -78.0~60.0 ℃ 、206.84 kPa 条件下， 反应 16.83h， 生成 (S)-4-[(3R,8R,9R,10S,13S,14R,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-pentanal
  参考文献：
  名称：

  First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

  摘要：

  We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00174-5