(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl-propionate

• 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)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl-propionate
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (2S)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoate
• 化学式: C₄₆H₆₂N₂O₄
• 分子量: 707.009
• InChiKey: XPTFWNKGZLORKU-SLDRDIAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  52
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-(1H-indol-3-ylmethyl)-2-oxoethyl]carbamate 、 胆固醇 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以84%的产率得到(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl-propionate
  参考文献：
  名称：

  Efficient microwave assisted access to chiral O-(α-protected-aminoacyl)steroids

  摘要：

  Chiral O-(alpha-protected-amino acyl)steroids 4a-f, 6a-b, 8 and 4a+4d and O-(alpha-protected-dipeptidoyl) steroids 12a,b are conveniently prepared under microwave irradiation in isolated yields of 65-96%, with complete chirality retention. The reaction utilized readily available N-(Z-alpha-aminoacyl)benzotriazoles 2a-f and Z-dipeptidoylbenzotriazole 11, with naturally occurring steroidal alcohols 3,5,7,9. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.04.003

文献信息

• Efficient microwave assisted access to chiral O-(α-protected-aminoacyl)steroids
  作者：Alan R. Katritzky、Parul Angrish

  DOI：10.1016/j.steroids.2006.04.003

  日期：2006.8

  Chiral O-(alpha-protected-amino acyl)steroids 4a-f, 6a-b, 8 and 4a+4d and O-(alpha-protected-dipeptidoyl) steroids 12a,b are conveniently prepared under microwave irradiation in isolated yields of 65-96%, with complete chirality retention. The reaction utilized readily available N-(Z-alpha-aminoacyl)benzotriazoles 2a-f and Z-dipeptidoylbenzotriazole 11, with naturally occurring steroidal alcohols 3,5,7,9. (c) 2006 Elsevier Inc. All rights reserved.