(1R,2S,13R,15R,16S)-4-hydroxy-13-(hydroxymethyl)-21-methoxy-22-(2-methoxyethoxymethoxy)-6,20-dimethyl-5-oxo-24-prop-2-enyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.02,14.04,12.07,11.018,23]tetracosa-6,11,18(23),19,21-pentaene-15-carbonitrile | 577747-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S,13R,15R,16S)-4-hydroxy-13-(hydroxymethyl)-21-methoxy-22-(2-methoxyethoxymethoxy)-6,20-dimethyl-5-oxo-24-prop-2-enyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.02,14.04,12.07,11.018,23]tetracosa-6,11,18(23),19,21-pentaene-15-carbonitrile
• CAS: 577747-87-6
• 化学式: C₃₂H₃₉N₃O₉
• 分子量: 609.676
• InChiKey: NMTNKMNYSUNHJO-YVYFGGICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (1R,2S,13R,15R,16S)-4-hydroxy-13-(hydroxymethyl)-21-methoxy-22-(2-methoxyethoxymethoxy)-6,20-dimethyl-5-oxo-24-prop-2-enyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.02,14.04,12.07,11.018,23]tetracosa-6,11,18(23),19,21-pentaene-15-carbonitrile 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
• 作为产物：
  描述：

  (1R,2S,13R,15R,16S)-22-hydroxy-13-(hydroxymethyl)-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 bis-triphenylphosphine-palladium(II) chloride 咪唑 、 4-二甲氨基吡啶 、 (PhSeO)2O 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium hydride 、 caesium carbonate 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 (1R,2S,13R,15R,16S)-4-hydroxy-13-(hydroxymethyl)-21-methoxy-22-(2-methoxyethoxymethoxy)-6,20-dimethyl-5-oxo-24-prop-2-enyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.02,14.04,12.07,11.018,23]tetracosa-6,11,18(23),19,21-pentaene-15-carbonitrile
  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