(25R)-3β-acetoxy-5α-spirost-23-en-3β-ol | 1100711-52-1

• 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: (25R)-3β-acetoxy-5α-spirost-23-en-3β-ol
• 英文别名: (25R)-5α-spirost-23-en-3β-ol acetate
• CAS: 1100711-52-1
• 化学式: C₂₉H₄₄O₄
• 分子量: 456.666
• InChiKey: DIQRRCJAXSZKET-OMRXZHHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  33.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (25R)-3β-acetoxy-5α-spirost-23-en-3β-ol 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以87%的产率得到(25S)-5α-spirost-23-ene-3β,25-diol 3-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
• 作为产物：
  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

文献信息

• On reactions of spirostane sapogenins with benzeneseleninic anhydride
  作者：Izabella Jastrzębska、Aneta Dobrogowska、Ewa Lutostańska、Jacek W. Morzycki

  DOI：10.1016/j.tet.2010.05.013

  日期：2010.7

  Direct dehydrogenation of spirostane sapogenins with benzeneseleninic anhydride/iodoxybenzene afforded the Δ22 derivatives in low yields. The reactions catalyzed by BF3/Et2O produced the 23-oxo-sapogenins in addition to their 22-oxo-23-spiro-isomers. The reactions of sapogenins with benzeneseleninic anhydride carried out in the presence of TiCl4 afforded products chlorinated at C23.

  与spirostane皂角苷配基的直接脱氢苯亚硒酸酐/ iodoxybenzene得到Δ 22在低的产率的衍生物。BF 3 / Et 2 O催化的反应除了生成22-oxo-23-spiro异构体外，还生成了23-oxo-sapogenins。皂苷元与苯硒二酸酐的反应在TiCl 4的存在下进行，得到在C23氯化的产物。
• On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids
  作者：Izabella Jastrzębska、Leszek Siergiejczyk、Aneta M. Tomkiel、Zofia Urbańczyk-Lipkowska、Dominik Wójcik、Jacek W. Morzycki

  DOI：10.1016/j.steroids.2009.02.010

  日期：2009.8

  The reaction of 23-oxotigogenin acetate with TMSOTf in THF afforded the corresponding bisnorcholanic lactone in 60% yield. The analogous reactions carried out in dichloromethane or benzene gave the rearranged products-the isometric spirostanic ketone (10-15%) and bisfuran (40-42%). Similar products were also obtained upon treatment of 23,24-epoxysapogenins with BF3. The epoxides treated with TiCl4 afforded mostly chlorohydrins and no rearranged products were detected. (C) 2009 Elsevier Inc. All rights reserved.