(2R,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-2-hydroxymethyl-piperidine

• 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: (2R,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-2-hydroxymethyl-piperidine
• 英文别名: methyl (2R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)piperidine-1-carboxylate
• 化学式: C₁₄H₂₉NO₄Si
• 分子量: 303.474
• InChiKey: GBTPGDHCXOSQSW-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5S)-methyl 5-(tert-butyldimethylsilanyloxy)-2-oxopiperidine-1-carboxylate 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 作用下， 以 甲苯 为溶剂， 反应 38.0h， 生成 (2R,5S)-5-t-butyldimethylsilyloxy-N-methoxycarbonyl-2-hydroxymethyl-piperidine
  参考文献：
  名称：

  Synthesis of 2S,5S-and 2R,5S-5-hydroxypipecolic acid via amide-methylenation of S-5-hydroxy-2-piperidone with dimethyltitanocene.

  摘要：

  A route to 2S,5S-and 2R,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselective methylenation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The transformation of the exocyclic enecarbamate double bond to the carboxylic acid group is best accomplished via hydroboration/oxidation to the alcohol 11a,b. Separation and oxidation of the diastereomers 11a,b, to 14a, and 14b, and hydrolysis furnishes the diastereomeric pipecolic acids 15a and 15b in enantiopure form.

  DOI：

  10.1016/s0957-4166(00)82257-0

文献信息

• Synthesis of 2S,5S-and 2R,5S-5-hydroxypipecolic acid via amide-methylenation of S-5-hydroxy-2-piperidone with dimethyltitanocene.
  作者：Claus Herdeis、Eberhard Heller

  DOI：10.1016/s0957-4166(00)82257-0

  日期：1993.1

  A route to 2S,5S-and 2R,5S-hydroxypipecolic acid is presented, starting with the enantiopure 5S-5-hydroxy-piperidone 7. The key step of this reaction sequence is the chemoselective methylenation of the amide carbonyl group of 8 with dimethyltitanocene 9 to 10. The transformation of the exocyclic enecarbamate double bond to the carboxylic acid group is best accomplished via hydroboration/oxidation to the alcohol 11a,b. Separation and oxidation of the diastereomers 11a,b, to 14a, and 14b, and hydrolysis furnishes the diastereomeric pipecolic acids 15a and 15b in enantiopure form.