((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 | 631920-74-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: ((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
• CAS: 631920-74-6
• 化学式: C₅₁H₅₆N₄O₉S
• 分子量: 901.093
• InChiKey: DLWZKLJGQDLTLG-CNKJTFKXSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  65.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  152.05
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  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 、 4-甲酰基-1-甲基吡咯碘化物 、 草酸 、 silica gel 、 sodium hydride 、 对甲苯磺酸 、 silver nitrate 、 溶剂黄146 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 生成 他比特啶
  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：

  (1R,2S,13R,15R,16S)-13-(aminomethyl)-22-hydroxy-21-methoxy-6,20,24-trimethyl-5-prop-2-enoxy-8,10-dioxa-14,24-diazahexacyclo[14.7.1.02,14.04,12.07,11.018,23]tetracosa-4,6,11,18(23),19,21-hexaene-15-carbonitrile 在 4-二甲氨基吡啶 、 potassium dihydrogenphosphate 、 磷酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 ((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
  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