1-[(1R,3S,5R,7S,9R,11S,14S,16S,17R,18R,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-9,18,21,27,29-pentamethyl-12-methylidene-35-[(2R)-3-[(2S,4R,5R)-4-methyl-5-[(2S)-4-(naphthalen-2-ylmethoxy)butan-2-yl]oxolan-2-yl]-2-(naphthalen-2-ylmethoxy)propyl]-17,34-bis(naphthalen-2-ylmethoxy)-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.03,20.05,18.07,16.09,14.027,41.029,39.031,37]tritetracont-22-en-11-yl]propan-2-one | 1388153-19-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[(1R,3S,5R,7S,9R,11S,14S,16S,17R,18R,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-9,18,21,27,29-pentamethyl-12-methylidene-35-[(2R)-3-[(2S,4R,5R)-4-methyl-5-[(2S)-4-(naphthalen-2-ylmethoxy)butan-2-yl]oxolan-2-yl]-2-(naphthalen-2-ylmethoxy)propyl]-17,34-bis(naphthalen-2-ylmethoxy)-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.03,20.05,18.07,16.09,14.027,41.029,39.031,37]tritetracont-22-en-11-yl]propan-2-one
• CAS: 1388153-19-2
• 化学式: C₉₉H₁₁₈O₁₅
• 分子量: 1548.02
• InChiKey: OTYSVKOVJJIFLG-CYOHEBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  114
• 可旋转键数：
  21
• 环数：
  18.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (S)-5-((3-((tert-butyldimethylsilyl)oxy)-2-methylpropyl)sulfonyl)-1-phenyl-1H-tetrazole 、 1-[(1R,3S,5R,7S,9R,11S,14S,16S,17R,18R,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-9,18,21,27,29-pentamethyl-12-methylidene-35-[(2R)-3-[(2S,4R,5R)-4-methyl-5-[(2S)-4-(naphthalen-2-ylmethoxy)butan-2-yl]oxolan-2-yl]-2-(naphthalen-2-ylmethoxy)propyl]-17,34-bis(naphthalen-2-ylmethoxy)-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.03,20.05,18.07,16.09,14.027,41.029,39.031,37]tritetracont-22-en-11-yl]propan-2-one 在 lithium diisopropyl amide 、 cerium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以53%的产率得到
  参考文献：
  名称：

  Total Synthesis and Complete Stereostructure of Gambieric Acid A

  摘要：

  Total synthesis of gambieric acid A, a potent antifungal polycyclic ether metabolite, has been accomplished for the first time, which firmly established the complete stereostructure of this natural product.

  DOI：

  10.1021/ja305864z
• 作为产物：
  描述：

  1-[(1R,3S,5R,7S,9R,11S,14S,16S,17R,18R,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-9,18,21,27,29-pentamethyl-12-methylidene-35-[(2R)-3-[(2S,4R,5R)-4-methyl-5-[(2S)-4-(naphthalen-2-ylmethoxy)butan-2-yl]oxolan-2-yl]-2-(naphthalen-2-ylmethoxy)propyl]-17,34-bis(naphthalen-2-ylmethoxy)-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.03,20.05,18.07,16.09,14.027,41.029,39.031,37]tritetracont-22-en-11-yl]propan-2-ol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以6.3 mg的产率得到1-[(1R,3S,5R,7S,9R,11S,14S,16S,17R,18R,20R,21R,22Z,25S,27R,29S,31R,34S,35R,37S,39R,41S)-9,18,21,27,29-pentamethyl-12-methylidene-35-[(2R)-3-[(2S,4R,5R)-4-methyl-5-[(2S)-4-(naphthalen-2-ylmethoxy)butan-2-yl]oxolan-2-yl]-2-(naphthalen-2-ylmethoxy)propyl]-17,34-bis(naphthalen-2-ylmethoxy)-2,6,10,15,19,26,30,36,40-nonaoxanonacyclo[23.18.0.03,20.05,18.07,16.09,14.027,41.029,39.031,37]tritetracont-22-en-11-yl]propan-2-one
  参考文献：
  名称：

  Total Synthesis and Complete Stereostructure of Gambieric Acid A

  摘要：

  Total synthesis of gambieric acid A, a potent antifungal polycyclic ether metabolite, has been accomplished for the first time, which firmly established the complete stereostructure of this natural product.

  DOI：

  10.1021/ja305864z