(5'S,6'S,8'R,9'R,10'R,11'S,12'R,14'S,17'R,20'S,26'S,27'S,30'R,31'R,32'S,33'R,35'S,38'R,41'S)-12',33'-bis[(3S)-4-hydroxy-3-methylbutyl]-5',9',11',26',30',32'-hexamethylspiro[1,3-dioxolane-2,29'-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaene]-8'-ol | 1010688-07-9

• 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: (5'S,6'S,8'R,9'R,10'R,11'S,12'R,14'S,17'R,20'S,26'S,27'S,30'R,31'R,32'S,33'R,35'S,38'R,41'S)-12',33'-bis[(3S)-4-hydroxy-3-methylbutyl]-5',9',11',26',30',32'-hexamethylspiro[1,3-dioxolane-2,29'-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaene]-8'-ol
• CAS: 1010688-07-9
• 化学式: C₅₆H₈₂N₂O₇
• 分子量: 895.276
• InChiKey: WDSMONRSWOSBRS-CDBPPFPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  65
• 可旋转键数：
  8
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 catechol-borane complex 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 以39%的产率得到(5'S,6'S,8'R,9'R,10'R,11'S,12'R,14'S,17'R,20'S,26'S,27'S,30'R,31'R,32'S,33'R,35'S,38'R,41'S)-12',33'-bis[(3S)-4-hydroxy-3-methylbutyl]-5',9',11',26',30',32'-hexamethylspiro[1,3-dioxolane-2,29'-13,34-dioxa-2,23-diazaundecacyclo[22.18.0.03,22.05,20.06,17.09,16.010,14.026,41.027,38.030,37.031,35]dotetraconta-1,3(22),15,23,36-pentaene]-8'-ol
  参考文献：
  名称：

  Chemo-, regio-, and stereoselectivity of F-ring opening reactions in the cephalostatin series

  摘要：

  In an effort to prepare unsymmetrical cephalostatin analogues with multi-functionality, we tried the route of selective opening of the spiroketal joining rings E and F. In this study, we have tested several borane complexes (like borane-9-BBN, borane-(N-tosyl)-D-valine, and borane-catechol) with some bis-steroidal pyrazine derivatives like 3, 4, and 16 aiming at opening ring-F at only one spiro-system of the dimer. Upon testing these borane reagents, satisfying results were obtained in the case of the ketomethylene 4 using the catechol-borane complex. The structures of the resulting mono-opened and also some double-opened spiro dimers have been completely confirmed. Some of the prepared compounds were tested against three cancer cell lines: HM02 (stomach cancer), HEP G2 (hepatocellular cancer), and MCF 7 (breast cancer). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.043

文献信息

• Chemo-, regio-, and stereoselectivity of F-ring opening reactions in the cephalostatin series
  作者：M. Nawasreh

  DOI：10.1016/j.bmc.2007.09.043

  日期：2008.1

  In an effort to prepare unsymmetrical cephalostatin analogues with multi-functionality, we tried the route of selective opening of the spiroketal joining rings E and F. In this study, we have tested several borane complexes (like borane-9-BBN, borane-(N-tosyl)-D-valine, and borane-catechol) with some bis-steroidal pyrazine derivatives like 3, 4, and 16 aiming at opening ring-F at only one spiro-system of the dimer. Upon testing these borane reagents, satisfying results were obtained in the case of the ketomethylene 4 using the catechol-borane complex. The structures of the resulting mono-opened and also some double-opened spiro dimers have been completely confirmed. Some of the prepared compounds were tested against three cancer cell lines: HM02 (stomach cancer), HEP G2 (hepatocellular cancer), and MCF 7 (breast cancer). (c) 2007 Elsevier Ltd. All rights reserved.