(E)-(20S,25R)-20,23-diacetyl-12-oxo-5α-furosta-22-ene-3β,26-diyl diacetate | 1129117-81-2

• 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: (E)-(20S,25R)-20,23-diacetyl-12-oxo-5α-furosta-22-ene-3β,26-diyl diacetate
• 英文别名: [(2R,4E)-4-[(1R,2S,4S,7S,8S,9S,12S,13S,16S,18S)-7-acetyl-16-acetyloxy-7,9,13-trimethyl-10-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosan-6-ylidene]-2-methyl-5-oxohexyl] acetate
• CAS: 1129117-81-2
• 化学式: C₃₅H₅₀O₈
• 分子量: 598.777
• InChiKey: QBOGYEBCAXVTDK-LKZRGCLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-(20S,25R)-20,23-diacetyl-12-oxo-5α-furosta-22-ene-3β,26-diyl diacetate 在 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-(25R)-23-acetyl-12-oxo-5α-furosat-22-ene-3β,26-diyl diacetate
  参考文献：
  名称：

  Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes

  摘要：

  We report the deacylation of (20R)-20-acetyl-23,24-dinorcholanic lactones by hydrazine hydrate, under microwave irradiation in high yields. The elimination of the 20-acetyl group proceeded with retention of configuration which contrast with other proved deacylation methods that yield a mixture of diastereoisomers. In this way, unnatural (20R)-23,24-dinorcholanic lactones can be produced rapidly on a large scale. Both (20R)- and (20S)-lactones were prepared starting from diosgenin, hecogenin and sarsasapogenin, in 72-80% overall yields. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.12.008
• 作为产物：
  描述：

  乙酸酐 、 海柯吉宁 在 Lewis acid 作用下， 生成 (E)-(20S,25R)-20,23-diacetyl-12-oxo-5α-furosta-22-ene-3β,26-diyl diacetate
  参考文献：
  名称：

  Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes

  摘要：

  We report the deacylation of (20R)-20-acetyl-23,24-dinorcholanic lactones by hydrazine hydrate, under microwave irradiation in high yields. The elimination of the 20-acetyl group proceeded with retention of configuration which contrast with other proved deacylation methods that yield a mixture of diastereoisomers. In this way, unnatural (20R)-23,24-dinorcholanic lactones can be produced rapidly on a large scale. Both (20R)- and (20S)-lactones were prepared starting from diosgenin, hecogenin and sarsasapogenin, in 72-80% overall yields. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.12.008

文献信息

• Novel steroidal penta- and hexacyclic compounds derived from 12-oxospirostan sapogenins
  作者：José Oscar H. Pérez-Díaz、José Luis Vega-Baez、Jesús Sandoval-Ramírez、Socorro Meza-Reyes、Sara Montiel-Smith、Norberto Farfán、Rosa Santillan

  DOI：10.1016/j.steroids.2010.07.008

  日期：2010.12

  The E ring regioselective acid-catalyzed opening of spirostanic sapogenins possessing a carbonyl group at C-12, such as botogenin and hecogenin, provided the new 12,23-cyclo-22,26-epoxycholesta-11,22-diene skeleton, in addition to new compounds of the already known 12,23-cyclocholest-12(23)-en-22-one frameworks. This transformation proceeds in a single step, under slightly acidic conditions. Both,

  E 环区域选择性酸催化打开在 C-12 处具有羰基的螺甾皂苷元，如肉毒杆菌素和 hecogenin，提供了新的 12,23-环-22,26-epoxycholesta-11,22-二烯骨架，此外已知的 12,23-cyclocholest-12(23)-en-22-one 骨架的新化合物。这种转化在弱酸性条件下一步进行。获得了五环和六环类固醇，同时保留了所有不对称中心的构型。