5-O'-tert-butyl 12-O'-methyl (4R,4'S,6'S,7'R)-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 | 1016976-28-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-O'-tert-butyl 12-O'-methyl (4R,4'S,6'S,7'R)-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
• CAS: 1016976-28-5
• 化学式: C₂₇H₂₈N₂O₈
• 分子量: 508.528
• InChiKey: YXUJCAILOSCIKM-WVIXRHDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  37
• 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：
  104
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-O'-tert-butyl 12-O'-methyl (4R,4'S,6'S,7'R)-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 碳酸氢钠 、 间氯过氧苯甲酸 、 乙酸酐 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 38.0h， 以52%的产率得到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
  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：

  三光气 、 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到5-O'-tert-butyl 12-O'-methyl (4R,4'S,6'S,7'R)-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
  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.