[(1R,2R,3R,11S,12R,14R,26R)-26-acetamido-12-cyano-5-hydroxy-6-methoxy-7,21,30-trimethyl-27-oxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaen-22-yl] acetate | 366020-46-4

• 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: [(1R,2R,3R,11S,12R,14R,26R)-26-acetamido-12-cyano-5-hydroxy-6-methoxy-7,21,30-trimethyl-27-oxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaen-22-yl] acetate
• CAS: 366020-46-4
• 化学式: C₃₃H₃₆N₄O₉S
• 分子量: 664.736
• InChiKey: LSGLBHRYSPDVFN-HUSLUMQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  47
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  185
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3R,11S,12R,14R,26R)-26-acetamido-12-cyano-5-hydroxy-6-methoxy-7,21,30-trimethyl-27-oxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaen-22-yl] acetate 在 copper(l) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以75%的产率得到ET-637
  参考文献：
  名称：

  Synthesis of Natural Ecteinascidins (ET-729, ET-745, ET-759B, ET-736, ET-637, ET-594) from Cyanosafracin B

  摘要：

  The semisynthetic process initially described for the synthesis of 1 (ET-743) has been extended to the preparation of other natural ecteinascidins. For the synthesis of 2 (ET-729) a demethylation of a N-Me intermediate was carried out by a selective oxidation with MCPBA. Other natural ecteinascidins (ET-745, ET-759B, ET-736, ET-637, ET-594) were accessible from key intermediate 25. The described methodologies allow for the preparation of a wide variety of ecteinascidins by procedures that can be easily scaled up.

  DOI：

  10.1021/jo034547i
• 作为产物：
  描述：

  ((6aS,7R,13S,14R,16R)-5-(allyloxy)-14-cyano-8-hydroxy-9-methoxy-4,10,17-trimethyl-6,6a,7,13,14,16-hexahydro-12H-7,13-epiminobenzo[4,5]azocino[1,2-b][1,3]dioxolo[4,5-h]isoquinolin-16-yl)methylS-((9H-fluoren-9-yl)methyl)-N-(tert-butoxycarbonyl)-L-cysteinate 在 bis-triphenylphosphine-palladium(II) chloride 三氟甲磺酸酐 、 (PhSeO)2O 、 三正丁基氢锡 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 0.5h， 生成 [(1R,2R,3R,11S,12R,14R,26R)-26-acetamido-12-cyano-5-hydroxy-6-methoxy-7,21,30-trimethyl-27-oxo-17,19,28-trioxa-24-thia-13,30-diazaheptacyclo[12.9.6.13,11.02,13.04,9.015,23.016,20]triaconta-4(9),5,7,15,20,22-hexaen-22-yl] acetate
  参考文献：
  名称：

  Synthesis of Natural Ecteinascidins (ET-729, ET-745, ET-759B, ET-736, ET-637, ET-594) from Cyanosafracin B

  摘要：

  The semisynthetic process initially described for the synthesis of 1 (ET-743) has been extended to the preparation of other natural ecteinascidins. For the synthesis of 2 (ET-729) a demethylation of a N-Me intermediate was carried out by a selective oxidation with MCPBA. Other natural ecteinascidins (ET-745, ET-759B, ET-736, ET-637, ET-594) were accessible from key intermediate 25. The described methodologies allow for the preparation of a wide variety of ecteinascidins by procedures that can be easily scaled up.

  DOI：

  10.1021/jo034547i

文献信息

• Synthesis of Natural Ecteinascidins (ET-729, ET-745, ET-759B, ET-736, ET-637, ET-594) from Cyanosafracin B
  作者：Roberto Menchaca、Valentín Martínez、Alberto Rodríguez、Natividad Rodríguez、María Flores、Pilar Gallego、Ignacio Manzanares、Carmen Cuevas

  DOI：10.1021/jo034547i

  日期：2003.11.1

  The semisynthetic process initially described for the synthesis of 1 (ET-743) has been extended to the preparation of other natural ecteinascidins. For the synthesis of 2 (ET-729) a demethylation of a N-Me intermediate was carried out by a selective oxidation with MCPBA. Other natural ecteinascidins (ET-745, ET-759B, ET-736, ET-637, ET-594) were accessible from key intermediate 25. The described methodologies allow for the preparation of a wide variety of ecteinascidins by procedures that can be easily scaled up.