tert-butyl (3S,6S,9R)-4-hydroxy-6-[(3-hydroxy-4-methoxy-5-methylphenyl)methyl]-2-methoxy-16-methyl-7-oxo-9-(phenylmethoxymethyl)-17-prop-2-enoxy-12,14-dioxa-5,8-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),10,15-triene-5-carboxylate | 1052707-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: tert-butyl (3S,6S,9R)-4-hydroxy-6-[(3-hydroxy-4-methoxy-5-methylphenyl)methyl]-2-methoxy-16-methyl-7-oxo-9-(phenylmethoxymethyl)-17-prop-2-enoxy-12,14-dioxa-5,8-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),10,15-triene-5-carboxylate
• CAS: 1052707-52-4
• 化学式: C₄₀H₄₈N₂O₁₁
• 分子量: 732.828
• InChiKey: VSCZXEZNJJPKGN-REFWIROBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,6S,9R)-4-hydroxy-6-[(3-hydroxy-4-methoxy-5-methylphenyl)methyl]-2-methoxy-16-methyl-7-oxo-9-(phenylmethoxymethyl)-17-prop-2-enoxy-12,14-dioxa-5,8-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),10,15-triene-5-carboxylate 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以69 mg的产率得到(1R,13R,16S)-20-hydroxy-21-methoxy-6,22-dimethyl-13-(phenylmethoxymethyl)-5-prop-2-enoxy-8,10-dioxa-14,24-diazahexacyclo[14.7.1.02,14.04,12.07,11.018,23]tetracosa-2,4,6,11,18,20,22-heptaen-15-one
  参考文献：
  名称：

  Synthetic Studies on Et-743. Assembly of the Pentacyclic Core and a Formal Total Synthesis

  摘要：

  A formal total synthesis of the potent anticancer agent Et-743 is described. The tetrahydroisoquinoline core is stereoselectively constructed using a novel radical cyclization of a glyoxalimine. Further elaboration of this core rapidly accessed the pentacyclic core of Et-743. but a mixture of regiosisomers was obtained in the key Pictet-Spengler ring closure. A known advanced intermediate in the synthesis of Et-743 was intercepted, constituting a formal synthesis of the molecule.

  DOI：

  10.1021/jo801159k
• 作为产物：
  描述：

  tert-butyl N-[(2S)-3-(3-hydroxy-4-methoxy-5-methylphenyl)-1-[(7R,9R)-7-(hydroxymethyl)-6-methoxy-4-methyl-9-(phenylmethoxymethyl)-5-prop-2-enoxy-7,9-dihydro-6H-[1,3]dioxolo[4,5-h]isoquinolin-8-yl]-1-oxopropan-2-yl]carbamate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 tert-butyl (3S,6S,9R)-4-hydroxy-6-[(3-hydroxy-4-methoxy-5-methylphenyl)methyl]-2-methoxy-16-methyl-7-oxo-9-(phenylmethoxymethyl)-17-prop-2-enoxy-12,14-dioxa-5,8-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1(17),10,15-triene-5-carboxylate
  参考文献：
  名称：

  Synthetic Studies on Et-743. Assembly of the Pentacyclic Core and a Formal Total Synthesis

  摘要：

  A formal total synthesis of the potent anticancer agent Et-743 is described. The tetrahydroisoquinoline core is stereoselectively constructed using a novel radical cyclization of a glyoxalimine. Further elaboration of this core rapidly accessed the pentacyclic core of Et-743. but a mixture of regiosisomers was obtained in the key Pictet-Spengler ring closure. A known advanced intermediate in the synthesis of Et-743 was intercepted, constituting a formal synthesis of the molecule.

  DOI：

  10.1021/jo801159k

文献信息

• Synthetic Studies on Et-743. Assembly of the Pentacyclic Core and a Formal Total Synthesis
  作者：Dan Fishlock、Robert M. Williams

  DOI：10.1021/jo801159k

  日期：2008.12.19

  A formal total synthesis of the potent anticancer agent Et-743 is described. The tetrahydroisoquinoline core is stereoselectively constructed using a novel radical cyclization of a glyoxalimine. Further elaboration of this core rapidly accessed the pentacyclic core of Et-743. but a mixture of regiosisomers was obtained in the key Pictet-Spengler ring closure. A known advanced intermediate in the synthesis of Et-743 was intercepted, constituting a formal synthesis of the molecule.