(1S,9S,11S,12R,14R,Z)-methyl 14-hydroxy-3-methyl-16-oxo-11-((triisopropylsilyl)oxy)-17,19-dioxatetracyclo[13.2.1.15,8.09,12]nonadeca-3,5,7,15(18)-tetraene-7-carboxylate | 1623756-02-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: (1S,9S,11S,12R,14R,Z)-methyl 14-hydroxy-3-methyl-16-oxo-11-((triisopropylsilyl)oxy)-17,19-dioxatetracyclo[13.2.1.15,8.09,12]nonadeca-3,5,7,15(18)-tetraene-7-carboxylate
• 英文别名: methyl (2S,4S,5R,7R,11S,13Z)-7-hydroxy-13-methyl-9-oxo-4-tri(propan-2-yl)silyloxy-10,18-dioxatetracyclo[13.2.1.18,11.02,5]nonadeca-1(17),8(19),13,15-tetraene-17-carboxylate
• CAS: 1623756-02-4
• 化学式: C₂₉H₄₂O₇Si
• 分子量: 530.734
• InChiKey: RNUUCXVHLLOTDT-DBIIQBLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,9S,11S,12R,14R,Z)-methyl 14-hydroxy-3-methyl-16-oxo-11-((triisopropylsilyl)oxy)-17,19-dioxatetracyclo[13.2.1.15,8.09,12]nonadeca-3,5,7,15(18)-tetraene-7-carboxylate 在 4-二甲氨基吡啶 、 i-Pr₄NOH 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Light-Mediated Total Synthesis of 17-Deoxyprovidencin

  摘要：

  AbstractAn asymmetric synthesis of the diterpenoid 17‐deoxyprovidencin is described. Key steps include an aldol addition, a base‐catalyzed Wipf‐type furan formation, a Z‐selective ring‐closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.

  DOI：

  10.1002/anie.201400617
• 作为产物：
  描述：

  methyl-2-((1S,2R,3S)-2-(2-hydroxy-2-((S)-5-(2-methylallyl)-2-oxo-2,5-dihydrofuran-3-yl)ethyl)-3-((triisopropylsilyl)oxy)cyclobutyl)-5-vinylfuran-3-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 苯 为溶剂， 反应 15.0h， 以46%的产率得到(1S,9S,11S,12R,14R,Z)-methyl 14-hydroxy-3-methyl-16-oxo-11-((triisopropylsilyl)oxy)-17,19-dioxatetracyclo[13.2.1.15,8.09,12]nonadeca-3,5,7,15(18)-tetraene-7-carboxylate
  参考文献：
  名称：

  Light-Mediated Total Synthesis of 17-Deoxyprovidencin

  摘要：

  AbstractAn asymmetric synthesis of the diterpenoid 17‐deoxyprovidencin is described. Key steps include an aldol addition, a base‐catalyzed Wipf‐type furan formation, a Z‐selective ring‐closing metathesis for macrocyclization, a photochemical E/Z isomerization to a highly strained and conformationally restricted ring system, and the stereoselective formation of two epoxides on the ring.

  DOI：

  10.1002/anie.201400617