(2S,3R)-N-tert-butoxycarbonyl-2-{(1R)-6-[(2S,3S)-N-tert-butoxycarbonyl-2-((1R)-1-methoxycarbonyl-hex-5-enyl)piperidin-3-yl]-1-methoxycarbonyl-hexyl}-3-vinyl-piperidine | 1255150-92-5

• 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: (2S,3R)-N-tert-butoxycarbonyl-2-{(1R)-6-[(2S,3S)-N-tert-butoxycarbonyl-2-((1R)-1-methoxycarbonyl-hex-5-enyl)piperidin-3-yl]-1-methoxycarbonyl-hexyl}-3-vinyl-piperidine
• 英文别名: tert-butyl (2S,3S)-3-[(6R)-6-[(2S,3R)-3-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-2-yl]-7-methoxy-7-oxoheptyl]-2-[(2R)-1-methoxy-1-oxohept-6-en-2-yl]piperidine-1-carboxylate
• CAS: 1255150-92-5
• 化学式: C₃₈H₆₄N₂O₈
• 分子量: 676.935
• InChiKey: SPNVEFGLIYSPMS-XPCOYVNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R)-N-tert-butoxycarbonyl-2-{(1R)-6-[(2S,3S)-N-tert-butoxycarbonyl-2-((1R)-1-methoxycarbonyl-hex-5-enyl)piperidin-3-yl]-1-methoxycarbonyl-hexyl}-3-vinyl-piperidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  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：

  (2S,3S)-N-tert-butoxycarbonyl-2-{(1R)-6-[(2S,3S)-N-tert-butoxycarbonyl-2-((1R)-1-methoxycarbonyl-5-oxo-pentyl)piperidin-3-yl]-1-methoxycarbonyl-hexyl}-3-formylpiperidine 、 甲基三苯基溴化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.34h， 以89%的产率得到(2S,3R)-N-tert-butoxycarbonyl-2-{(1R)-6-[(2S,3S)-N-tert-butoxycarbonyl-2-((1R)-1-methoxycarbonyl-hex-5-enyl)piperidin-3-yl]-1-methoxycarbonyl-hexyl}-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

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.