methyl (8S,9S,10R,11S,13S,14S,17R)-10,13-dimethyl-3-oxo-11,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate | 1104412-80-7

• 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: methyl (8S,9S,10R,11S,13S,14S,17R)-10,13-dimethyl-3-oxo-11,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
• CAS: 1104412-80-7
• 化学式: C₂₇H₄₄O₅Si₂
• 分子量: 504.814
• InChiKey: NNSCZQKPMBVBTM-QYOSXDNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.89
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (8S,9S,10R,11S,13S,14S,17R)-10,13-dimethyl-3-oxo-11,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 以99%的产率得到methyl (8S,9S,10R,11S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-11-trimethylsilyloxy-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
  参考文献：
  名称：

  A highly selective method for 11β-OH protection of steroidal 11β, 17α-diols

  摘要：

  A highly selective method to protect the 11 beta-OH position of steroid (1) has been developed. This is achieved via double silyl protection of the 11 beta, 17 alpha-diol, followed by selective desilylation of the 17 alpha-OH under basic conditions without the need for a fluoride source. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.01.016
• 作为产物：
  描述：

  三甲基氯硅烷 、 Δ1-CA-Me 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以30.9 g的产率得到methyl (8S,9S,10R,11S,13S,14S,17R)-10,13-dimethyl-3-oxo-11,17-bis(trimethylsilyloxy)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
  参考文献：
  名称：

  A highly selective method for 11β-OH protection of steroidal 11β, 17α-diols

  摘要：

  A highly selective method to protect the 11 beta-OH position of steroid (1) has been developed. This is achieved via double silyl protection of the 11 beta, 17 alpha-diol, followed by selective desilylation of the 17 alpha-OH under basic conditions without the need for a fluoride source. (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2008.01.016

文献信息

• A highly selective method for 11β-OH protection of steroidal 11β, 17α-diols
  作者：Paul A. Glossop、Marcel Hoogenraad、Torren M. Peakman、Dannielle F. Roberts

  DOI：10.1016/j.steroids.2008.01.016

  日期：2008.5

  A highly selective method to protect the 11 beta-OH position of steroid (1) has been developed. This is achieved via double silyl protection of the 11 beta, 17 alpha-diol, followed by selective desilylation of the 17 alpha-OH under basic conditions without the need for a fluoride source. (C) 2008 Elsevier Inc. All rights reserved.