(2S,3S)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-[(1R)-1-(ethylthio)carbonyl-but-3-enyl]piperidine | 1255150-79-8

• 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,3S)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-[(1R)-1-(ethylthio)carbonyl-but-3-enyl]piperidine
• 英文别名: tert-butyl (2S,3S)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(2R)-1-ethylsulfanyl-1-oxopent-4-en-2-yl]piperidine-1-carboxylate
• CAS: 1255150-79-8
• 化学式: C₂₄H₄₅NO₄SSi
• 分子量: 471.777
• InChiKey: WCFBGHIYBWBXGS-AQNXPRMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-[(1R)-1-(ethylthio)carbonyl-but-3-enyl]piperidine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到(2R,3S)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-[(1R)-1-hydroxymethyl-but-3-enyl]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：

  (Z)-(1-[ethylthio]penta-1,4-dienyloxy)trimethylsilane 、 (3R)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-hydroxy-piperidine 在 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以57%的产率得到(2S,3S)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-[(1R)-1-(ethylthio)carbonyl-but-3-enyl]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.