tert-butyl ((S)-1-((4R,5aR,9aS)-10-(allyloxy)-4-((allyloxy)methyl)-8,8,11-trimethyl-4,5a,6,9a-tetrahydro-5H-[1,3]dioxino[5,4-c][1,3]dioxolo[4,5-h]isoquinolin-5-yl)-3-(3-hydroxy-4-methoxy-5-methylphenyl)-1-oxopropan-2-yl)carbamate | 1052707-90-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl ((S)-1-((4R,5aR,9aS)-10-(allyloxy)-4-((allyloxy)methyl)-8,8,11-trimethyl-4,5a,6,9a-tetrahydro-5H-[1,3]dioxino[5,4-c][1,3]dioxolo[4,5-h]isoquinolin-5-yl)-3-(3-hydroxy-4-methoxy-5-methylphenyl)-1-oxopropan-2-yl)carbamate
• CAS: 1052707-90-0
• 化学式: C₃₈H₅₀N₂O₁₁
• 分子量: 710.822
• InChiKey: NZHNTBDJZKLYPQ-GMNHBYEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.73
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  143.48
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tert-butyl ((S)-1-((4R,5aR,9aS)-10-(allyloxy)-4-((allyloxy)methyl)-8,8,11-trimethyl-4,5a,6,9a-tetrahydro-5H-[1,3]dioxino[5,4-c][1,3]dioxolo[4,5-h]isoquinolin-5-yl)-3-(3-hydroxy-4-methoxy-5-methylphenyl)-1-oxopropan-2-yl)carbamate 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以91%的产率得到tert-butyl ((S)-1-((4R,5aR,9aS)-10-(allyloxy)-4-((allyloxy)methyl)-8,8,11-trimethyl-4,5a,6,9a-tetrahydro-5H-[1,3]dioxino[5,4-c][1,3]dioxolo[4,5-h]isoquinolin-5-yl)-3-(3-((tert-butoxycarbonyl)oxy)-4-methoxy-5-methylphenyl)-1-oxopropan-2-yl)carbamate
  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-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-5-methylphenyl]-1-oxo-1-[(2S,7R,9R)-4,4,16-trimethyl-17-prop-2-enoxy-9-(prop-2-enoxymethyl)-3,5,12,14-tetraoxa-8-azatetracyclo[8.7.0.02,7.011,15]heptadeca-1(17),10,15-trien-8-yl]propan-2-yl]carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以90%的产率得到tert-butyl ((S)-1-((4R,5aR,9aS)-10-(allyloxy)-4-((allyloxy)methyl)-8,8,11-trimethyl-4,5a,6,9a-tetrahydro-5H-[1,3]dioxino[5,4-c][1,3]dioxolo[4,5-h]isoquinolin-5-yl)-3-(3-hydroxy-4-methoxy-5-methylphenyl)-1-oxopropan-2-yl)carbamate
  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