[(1R,2R,3R,11S,12R,14R,26R)-12-cyano-6-methoxy-5-(2-methoxyethoxymethoxy)-7,21-dimethyl-26-[(2-methylpropan-2-yl)oxycarbonylamino]-27-oxo-30-prop-2-enyl-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 | 577747-89-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: [(1R,2R,3R,11S,12R,14R,26R)-12-cyano-6-methoxy-5-(2-methoxyethoxymethoxy)-7,21-dimethyl-26-[(2-methylpropan-2-yl)oxycarbonylamino]-27-oxo-30-prop-2-enyl-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: 577747-89-8
• 化学式: C₄₂H₅₂N₄O₁₂S
• 分子量: 836.96
• InChiKey: XOBLUPKMSXIRIC-KHWGGRFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  59
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  202
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3R,11S,12R,14R,26R)-12-cyano-6-methoxy-5-(2-methoxyethoxymethoxy)-7,21-dimethyl-26-[(2-methylpropan-2-yl)oxycarbonylamino]-27-oxo-30-prop-2-enyl-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 4-甲酰基-1-甲基吡咯碘化物 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.75h， 生成 [(1R,2R,3R,11S,12R,14R)-12-cyano-5-hydroxy-6-methoxy-7,21-dimethyl-26,27-dioxo-30-prop-2-enyl-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
• 作为产物：
  描述：

  N-Α-叔丁氧羰基-S-(9-芴甲基)-L-半胱氨酸 在 4-二甲氨基吡啶 、 三氟甲磺酸酐 、 二甲基亚砜 、 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 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 [(1R,2R,3R,11S,12R,14R,26R)-12-cyano-6-methoxy-5-(2-methoxyethoxymethoxy)-7,21-dimethyl-26-[(2-methylpropan-2-yl)oxycarbonylamino]-27-oxo-30-prop-2-enyl-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