2,2,2-trichloroethyl (2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(furan-3-yl)-3-methyl-4-oxopiperidine-1-carboxylate | 209160-53-2

• 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: 2,2,2-trichloroethyl (2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(furan-3-yl)-3-methyl-4-oxopiperidine-1-carboxylate
• CAS: 209160-53-2
• 化学式: C₂₀H₃₀Cl₃NO₅Si
• 分子量: 498.906
• InChiKey: VKZJCGARTOFMQI-BPUTZDHNSA-N

物化性质

• 沸点：
  500.946±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.212±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(furan-3-yl)-3-methyl-4-oxopiperidine-1-carboxylate 在 ruthenium trichloride 、 sodium periodate 、 溶剂黄146 、 锌 作用下， 以 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (2S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-4-oxo-piperidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414
• 作为产物：
  描述：

  (2R,3S,6S)-6-Furan-3-yl-2-hydroxymethyl-3-methyl-piperidin-4-one 在 吡啶 、 咪唑 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 2,2,2-trichloroethyl (2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(furan-3-yl)-3-methyl-4-oxopiperidine-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives

  摘要：

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.

  DOI：

  10.1021/jo9722414

文献信息

• Enantioselective Synthesis of Substituted Pipecolic Acid Derivatives
  作者：José Barluenga、Fernando Aznar、Carlos Valdés、Cristina Ribas

  DOI：10.1021/jo9722414

  日期：1998.6.1

  Enantiomerically pure 4-piperidones, prepared by asymmetric [4 + 2] Diels-Alder cycloadditon of chiral 2-aminodienes with imines, have been used as starting materials for the synthesis of several derivatives of pipecolic acid. The alpha-amino acid moiety is obtained after the oxidation of a hydroxy group or a furan ring of a conveniently protected 2-aryl-6-(hydroxymethyl)-4-piperidone. Depending on the starting piperidone and the synthetic strategy, it is possible to obtain D- or L-functionalized pipecolic acid derivatives by a short synthetic procedure. Moreover, a stereoselective epimerization of the alpha-carbon atom of a particular pipecolate allows for the preparation of both cis- and trans-6-(hydroxymethyl)pipecolic acids, structures related with dipeptide isosteres.