(2R)-2-[(3R,8S,9R,10S,13R,14R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-ol | 221454-11-1

• 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: (2R)-2-[(3R,8S,9R,10S,13R,14R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-ol
• CAS: 221454-11-1
• 化学式: C₃₃H₅₈O₂Si
• 分子量: 514.908
• InChiKey: AKXHJYYENAPABK-FQQDXQEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.31
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(3R,8S,9R,10S,13R,14R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-ol 在 platinum on activated charcoal 吡啶 、 四丁基氟化铵 、 氢气 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 ent-cholesterol
  参考文献：
  名称：

  A new method for the preparation of ent-cholesterol from ent-testosterone

  摘要：

  An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C-21 3-silyloxy-Delta(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Delta(16) double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent-testosterone (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02588-x
• 作为产物：
  描述：

  4-甲基戊醛 、 ent-3-O-[(1,1-Dimethylethyl)dimethylsilyl]-(3β,17Z)-pregna-5,17(20)-dien-3-ol 在 氯化二乙基铝 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-2-[(3R,8S,9R,10S,13R,14R)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-ol
  参考文献：
  名称：

  A new method for the preparation of ent-cholesterol from ent-testosterone

  摘要：

  An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C-21 3-silyloxy-Delta(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Delta(16) double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent-testosterone (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02588-x

文献信息

• A new method for the preparation of ent-cholesterol from ent-testosterone
  作者：A.Sampath Kumar、Douglas F. Covey

  DOI：10.1016/s0040-4039(98)02588-x

  日期：1999.1

  An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C-21 3-silyloxy-Delta(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Delta(16) double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent-testosterone (C) 1999 Elsevier Science Ltd. All rights reserved.