11-O'-tert-butyl 4-O'-methyl (4S,9'R,10'S,12'S)-9'-hydroxy-2-oxo-6'-phenylmethoxyspiro[1,3-dioxolane-4,8'-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-triene]-4',11'-dicarboxylate | 1016976-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 11-O'-tert-butyl 4-O'-methyl (4S,9'R,10'S,12'S)-9'-hydroxy-2-oxo-6'-phenylmethoxyspiro[1,3-dioxolane-4,8'-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-triene]-4',11'-dicarboxylate
• CAS: 1016976-31-0
• 化学式: C₂₇H₂₈N₂O₁₀
• 分子量: 540.527
• InChiKey: JPBBHINOZRFPPO-SERDRRHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  11-O'-tert-butyl 4-O'-methyl (4S,9'R,10'S,12'S)-9'-hydroxy-2-oxo-6'-phenylmethoxyspiro[1,3-dioxolane-4,8'-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-triene]-4',11'-dicarboxylate 在 10% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以100%的产率得到11-O'-tert-butyl 4-O'-methyl (4S,9'R,10'S,12'S)-6',9'-dihydroxy-2-oxospiro[1,3-dioxolane-4,8'-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-triene]-4',11'-dicarboxylate
  参考文献：
  名称：

  Synthesis of 7-Epi (+)-FR900482:  An Epimer of Comparable Anti-Cancer Activity

  摘要：

  FR900482 is a potent anti-tumor therapeutic that has been investigated as a replacement candidate for the clinically useful Mitomycin C. Herein, we report synthesis and biological testing of 7-Epi (+)-FR900482, which demonstrates equal potency relative to the natural product against several cancer cell lines. Highlights of this work include utilization of our palladium-catalyzed DYKAT methodology and development of a Polonovski oxidative ring expansion strategy to yield this equipotent epimer in 23 linear steps.

  DOI：

  10.1021/ol800127a
• 作为产物：
  描述：

  5-O'-tert-butyl 12-O'-methyl (4S,4'S,6'S,7'S)-7'-hydroxy-2-oxo-10'-phenylmethoxyspiro[1,3-dioxolane-4,8'-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),10,12-triene]-5',12'-dicarboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 11-O'-tert-butyl 4-O'-methyl (4S,9'R,10'S,12'S)-9'-hydroxy-2-oxo-6'-phenylmethoxyspiro[1,3-dioxolane-4,8'-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-triene]-4',11'-dicarboxylate 、
  参考文献：
  名称：

  Synthesis of 7-Epi (+)-FR900482:  An Epimer of Comparable Anti-Cancer Activity

  摘要：

  FR900482 is a potent anti-tumor therapeutic that has been investigated as a replacement candidate for the clinically useful Mitomycin C. Herein, we report synthesis and biological testing of 7-Epi (+)-FR900482, which demonstrates equal potency relative to the natural product against several cancer cell lines. Highlights of this work include utilization of our palladium-catalyzed DYKAT methodology and development of a Polonovski oxidative ring expansion strategy to yield this equipotent epimer in 23 linear steps.

  DOI：

  10.1021/ol800127a

文献信息

• Synthesis of 7-<i>Epi</i> (+)-FR900482:  An Epimer of Comparable Anti-Cancer Activity
  作者：Barry M. Trost、Brendan M. O'Boyle

  DOI：10.1021/ol800127a

  日期：2008.4.1

  FR900482 is a potent anti-tumor therapeutic that has been investigated as a replacement candidate for the clinically useful Mitomycin C. Herein, we report synthesis and biological testing of 7-Epi (+)-FR900482, which demonstrates equal potency relative to the natural product against several cancer cell lines. Highlights of this work include utilization of our palladium-catalyzed DYKAT methodology and development of a Polonovski oxidative ring expansion strategy to yield this equipotent epimer in 23 linear steps.