(3R)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-hydroxy-piperidine | 1255150-68-5

• 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: (3R)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-hydroxy-piperidine
• 英文别名: tert-butyl (3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-hydroxypiperidine-1-carboxylate
• CAS: 1255150-68-5
• 化学式: C₁₇H₃₅NO₄Si
• 分子量: 345.555
• InChiKey: MDICQLDVRNGHSX-KWCCSABGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allylketene methyl trimethylsilyl acetal 、 (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46%的产率得到(2S,3S)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-[(1S)-1-methoxycarbonyl-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：

  (4S)-N-tert-butoxycarbonyl-4-((tert-butyldimethylsiloxy)methyl)-5-hydroxypentylamine 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以72%的产率得到(3R)-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-2-hydroxy-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.