(2S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-4-oxo-piperidine-1,2-dicarboxylic acid 2-methyl ester 1-(2,2,2-trichloro-ethyl) ester | 209160-27-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-4-oxo-piperidine-1,2-dicarboxylic acid 2-methyl ester 1-(2,2,2-trichloro-ethyl) ester
• 英文别名: 2-O-methyl 1-O-(2,2,2-trichloroethyl) (2S,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methyl-4-oxopiperidine-1,2-dicarboxylate
• CAS: 209160-27-0
• 化学式: C₁₈H₃₀Cl₃NO₆Si
• 分子量: 490.884
• InChiKey: YUUDNDAGCUKUNL-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-4-oxo-piperidine-1,2-dicarboxylic acid 2-methyl ester 1-(2,2,2-trichloro-ethyl) ester 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以99%的产率得到(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)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(furan-3-yl)-3-methylpiperidin-4-one 在 吡啶 、 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 (2S,5S,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-4-oxo-piperidine-1,2-dicarboxylic acid 2-methyl ester 1-(2,2,2-trichloro-ethyl) 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