[(1S,2S,4R,5S,6S,9S,10S,13R,15R,18S)-6-(1-acetyloxyethyl)-5,18-dimethyl-3-(2-trimethylsilylethylsulfonyl)-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-yl] acetate | 304641-96-1

• 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: [(1S,2S,4R,5S,6S,9S,10S,13R,15R,18S)-6-(1-acetyloxyethyl)-5,18-dimethyl-3-(2-trimethylsilylethylsulfonyl)-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-yl] acetate
• CAS: 304641-96-1
• 化学式: C₃₀H₅₁NO₆SSi
• 分子量: 581.89
• InChiKey: VXOQMSZLJMDJJT-VEXFCCATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  苯硫酚 、 [(1S,2S,4R,5S,6S,9S,10S,13R,15R,18S)-6-(1-acetyloxyethyl)-5,18-dimethyl-3-(2-trimethylsilylethylsulfonyl)-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-yl] acetate 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以47%的产率得到Acetic acid 1-((3R,5R,8S,10S,12S,13S,14S,17S)-3-acetoxy-10,13-dimethyl-12-phenylsulfanyl-2,3,4,5,6,7,8,10,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester
  参考文献：
  名称：

  Aziridination of 11-pregnene-3,20-dione using PhIN-Ses

  摘要：

  The copper-catalyzed reaction of [N-(Ses)imino]phenyliodinane with 11-pregnene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses protecting group could be conveniently removed using the TASF reagent. Furthermore, nucleophilic ring opening of the protected N-Ses-aziridine with thiophenol in the presence of a Lewis acid led to introduction of the thiophenol group at the alpha-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01228-4
• 作为产物：
  描述：

  N-[2-(trimethylsilyl)ethanesulfonyl]-11α,12α-aziridino-5β-H-pregnane-3,20-dione 在 吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 24.25h， 生成 [(1S,2S,4R,5S,6S,9S,10S,13R,15R,18S)-6-(1-acetyloxyethyl)-5,18-dimethyl-3-(2-trimethylsilylethylsulfonyl)-3-azapentacyclo[8.8.0.02,4.05,9.013,18]octadecan-15-yl] acetate
  参考文献：
  名称：

  Aziridination of 11-pregnene-3,20-dione using PhIN-Ses

  摘要：

  The copper-catalyzed reaction of [N-(Ses)imino]phenyliodinane with 11-pregnene-3,20-dione gave the corresponding aziridine in 53% yield. The Ses protecting group could be conveniently removed using the TASF reagent. Furthermore, nucleophilic ring opening of the protected N-Ses-aziridine with thiophenol in the presence of a Lewis acid led to introduction of the thiophenol group at the alpha-12 position but, unexpectedly, concomitant loss of the Ses group to provide compound 10. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01228-4