tert-butyl (2S,3S)-3-[(6R)-6-[(2S,3R)-3-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]-7-hydroxy-8-methylnon-8-enyl]-2-[(4R)-3-hydroxy-2-methylnona-1,8-dien-4-yl]piperidine-1-carboxylate | 1255151-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: tert-butyl (2S,3S)-3-[(6R)-6-[(2S,3R)-3-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]-7-hydroxy-8-methylnon-8-enyl]-2-[(4R)-3-hydroxy-2-methylnona-1,8-dien-4-yl]piperidine-1-carboxylate
• CAS: 1255151-06-4
• 化学式: C₄₂H₇₂N₂O₆
• 分子量: 701.043
• InChiKey: DJKYKXGIJADJOO-SUIGPBQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-[(6R)-6-[(2S,3R)-3-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]-7-hydroxy-8-methylnon-8-enyl]-2-[(4R)-3-hydroxy-2-methylnona-1,8-dien-4-yl]piperidine-1-carboxylate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以205 mg的产率得到(2S,3R)-N-tert-butoxycarbonyl-2-{(4R)-9-[(2S,3S)-N-tert-butoxycarbonyl-2-((4R)-2-methyl-3-oxonona-1,8-dien-4-yl)piperidin-3-yl]-2-methyl-3-oxonon-1-en-4-yl}-3-vinyl-piperidine
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)- and (+)-Petrosin

  摘要：

  The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.

  DOI：

  10.1021/ol1022257
• 作为产物：
  描述：

  tert-butyl (2S,3R)-2-((R)-7-((2S,3S)-1-(tert-butoxycarbonyl)-2-((R)-1-oxohept-6-en-2-yl)piperidin-3-yl)-1-oxoheptan-2-yl)-3-vinylpiperidine-1-carboxylate 、 异丙烯基溴化镁 在 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl (2S,3S)-3-[(6R)-6-[(2S,3R)-3-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]-7-hydroxy-8-methylnon-8-enyl]-2-[(4R)-3-hydroxy-2-methylnona-1,8-dien-4-yl]piperidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)- and (+)-Petrosin

  摘要：

  The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.

  DOI：

  10.1021/ol1022257

文献信息

• Enantioselective Total Synthesis of (−)- and (+)-Petrosin
  作者：Hiroki Toya、Kentaro Okano、Kiyosei Takasu、Masataka Ihara、Atsushi Takahashi、Haruo Tanaka、Hidetoshi Tokuyama

  DOI：10.1021/ol1022257

  日期：2010.11.19

  The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.