(2E,10E,12E,16Z,18E)-(5S,6R,7S,9S,15R)-6-(tert-Butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-19-((2S,3S)-6-hydroxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3,5,7,11,15-pentamethyl-9-triisopropylsilanyloxymethyl-nonadeca-2,10,12,16,18-pentaen-8-one | 753016-61-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,10E,12E,16Z,18E)-(5S,6R,7S,9S,15R)-6-(tert-Butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-19-((2S,3S)-6-hydroxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3,5,7,11,15-pentamethyl-9-triisopropylsilanyloxymethyl-nonadeca-2,10,12,16,18-pentaen-8-one
• CAS: 753016-61-4
• 化学式: C₄₈H₈₆O₆Si₂
• 分子量: 815.378
• InChiKey: SZLKPTPFXONETQ-TVCOCKOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.69
• 重原子数：
  56.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2E,10E,12E,16Z,18E)-(5S,6R,7S,9S,15R)-6-(tert-Butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-19-((2S,3S)-6-hydroxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3,5,7,11,15-pentamethyl-9-triisopropylsilanyloxymethyl-nonadeca-2,10,12,16,18-pentaen-8-one 在 吡啶 、 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以49%的产率得到(2E,10E,12E,16Z,18E)-(5S,6R,7S,9S,15R)-6-(tert-Butyl-dimethyl-silanyloxy)-17-ethyl-3,5,7,11,15-pentamethyl-19-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-8-oxo-9-triisopropylsilanyloxymethyl-nonadeca-2,10,12,16,18-pentaenal
  参考文献：
  名称：

  First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination

  摘要：

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.

  DOI：

  10.1021/ol049219z
• 作为产物：
  描述：

  [(2E,5S,6R,7S,9S,10E,12E,15R,16Z,18E)-6-[tert-butyl(dimethyl)silyl]oxy-17-ethyl-19-[(2S,3S)-6-methoxy-3-methyl-3,6-dihydro-2H-pyran-2-yl]-3,5,7,11,15-pentamethyl-8-oxo-9-[tri(propan-2-yl)silyloxymethyl]nonadeca-2,10,12,16,18-pentaenyl] prop-2-enyl carbonate 在 四(三苯基膦)钯 4-甲基苯磺酸吡啶 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 29.5h， 生成 (2E,10E,12E,16Z,18E)-(5S,6R,7S,9S,15R)-6-(tert-Butyl-dimethyl-silanyloxy)-17-ethyl-1-hydroxy-19-((2S,3S)-6-hydroxy-3-methyl-3,6-dihydro-2H-pyran-2-yl)-3,5,7,11,15-pentamethyl-9-triisopropylsilanyloxymethyl-nonadeca-2,10,12,16,18-pentaen-8-one
  参考文献：
  名称：

  First Total Synthesis of the Antitumor Compound (−)-Kazusamycin A and Absolute Structure Determination

  摘要：

  The first total synthesis of kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.

  DOI：

  10.1021/ol049219z