(2S,3S)-2-[(1R)-5-benzyloxy-1-methoxycarbonyl-pentyl]-N-tert-butoxycarbonyl-3-hydroxymethyl-piperidine | 1255150-85-6

• 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)-2-[(1R)-5-benzyloxy-1-methoxycarbonyl-pentyl]-N-tert-butoxycarbonyl-3-hydroxymethyl-piperidine
• CAS: 1255150-85-6
• 化学式: C₂₅H₃₉NO₆
• 分子量: 449.588
• InChiKey: ICXCQNWREOXXFA-VSKRKVRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-[(1R)-5-benzyloxy-1-methoxycarbonyl-pentyl]-N-tert-butoxycarbonyl-3-hydroxymethyl-piperidine 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 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)-2-[(1R)-5-benzyloxy-1-methoxycarbonyl-pentyl]-N-tert-butoxycarbonyl-3-((tert-butyldimethylsiloxy)methyl)-piperidine 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以100%的产率得到(2S,3S)-2-[(1R)-5-benzyloxy-1-methoxycarbonyl-pentyl]-N-tert-butoxycarbonyl-3-hydroxymethyl-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