(2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10S,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-3'-(2-tosylhydrazineylidene)docosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl acetate | 1100711-64-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10S,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-3'-(2-tosylhydrazineylidene)docosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl acetate
• CAS: 1100711-64-5
• 化学式: C₃₆H₅₂N₂O₆S
• 分子量: 640.885
• InChiKey: JUMGGQPGIAIPQX-RGADGNKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  45.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  103.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10S,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-3'-(2-tosylhydrazineylidene)docosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl acetate 在 lithium hydride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以39%的产率得到(25R)-3β-acetoxy-5α-spirost-23-en-3β-ol
  参考文献：
  名称：

  Synthesis of “glycospirostanes”—Steroid sapogenins with a sugar-like ring F

  摘要：

  The synthesis of two "glycospirostanes" from 23-oxotigogenin acetate is described. (23S,24S,25R)-5 alpha-Spirostane-3 beta,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OSO4 dihydroxylation of the C24-C25 double bond. Allylic hydroxylation with SeO2 of 3 beta-acetoxy-5 alpha-spirost-23-ene obtained from 23-oxotigogenin acetate followed by OSO4 dihydroxylation of the C23-C24 double bond afforded (23R,24S,25R)-5 alpha-spirostane-3 beta,23,24,25-tetraol. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.12.015
• 作为产物：
  描述：

  对甲苯磺酰肼 、 23-oxotigogenin acetate 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (2aS,4S,5'R,6aS,6bS,8aS,8bR,9S,10S,11aS,12aS,12bR)-5',6a,8a,9-tetramethyl-3'-(2-tosylhydrazineylidene)docosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl acetate
  参考文献：
  名称：

  Synthesis of “glycospirostanes”—Steroid sapogenins with a sugar-like ring F

  摘要：

  The synthesis of two "glycospirostanes" from 23-oxotigogenin acetate is described. (23S,24S,25R)-5 alpha-Spirostane-3 beta,23,24,25-tetraol was obtained by dehydrogenation followed by stereoselective reduction of the 23-oxo group and OSO4 dihydroxylation of the C24-C25 double bond. Allylic hydroxylation with SeO2 of 3 beta-acetoxy-5 alpha-spirost-23-ene obtained from 23-oxotigogenin acetate followed by OSO4 dihydroxylation of the C23-C24 double bond afforded (23R,24S,25R)-5 alpha-spirostane-3 beta,23,24,25-tetraol. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.12.015