(3R,4S)-N-tert-butyloxycarbonyl-4-hydroxypiperidine-3-carboxylic acid methyl ester | 309918-19-2

• 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: (3R,4S)-N-tert-butyloxycarbonyl-4-hydroxypiperidine-3-carboxylic acid methyl ester
• 英文别名: 1-O-tert-butyl 3-O-methyl (3R,4S)-4-hydroxypiperidine-1,3-dicarboxylate
• CAS: 309918-19-2
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: OULNMKPQUKNAHO-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 (3R,4S)-N-tert-butyloxycarbonyl-4-hydroxypiperidine-3-carboxylic acid methyl ester 在 sodium carbonate 作用下， 反应 5.0h， 以86%的产率得到(+/-)-ethyl cis-1-(tert-butoxycarbonyl)-4-hydroxypiperidine-3-carboxylate
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Isogalactofagomine

  摘要：

  A new chemoenzymatic synthesis of optically pure isogalactofagomine 2 starting from achiral starting materials is presented. Dimethyl 4-hydroxypyridine-3,5-dicarboxylate (7) was synthesized and converted to the corresponding saturated piperidine 8. Then the key step of the synthesis was carried out: Lipase M catalyzed hydrolysis of the prochiral diester 8 to cause formation of an asymmetric monoacid with at least 98% enantiomeric excess. Reduction of the acid, saponification of the remaining ester, and radical iododecarboxylation gave an iodide that after substitution with silver trifluoroacetate and hydrolysis gave 2.

  DOI：

  10.1021/jo000699r
• 作为产物：
  描述：

  (3,4-cis-4,5-cis)-N-tert-butyloxycarbonyl-4-hydroxypiperidine-3,5-dicarboxylic acid dimethyl ester 在 N-甲基吗啉 、 氯甲酸乙酯 、 叔丁基硫醇 、 三乙胺 、 subtilisin Carlsberg 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 216.66h， 生成 (3R,4S)-N-tert-butyloxycarbonyl-4-hydroxypiperidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Isogalactofagomine

  摘要：

  A new chemoenzymatic synthesis of optically pure isogalactofagomine 2 starting from achiral starting materials is presented. Dimethyl 4-hydroxypyridine-3,5-dicarboxylate (7) was synthesized and converted to the corresponding saturated piperidine 8. Then the key step of the synthesis was carried out: Lipase M catalyzed hydrolysis of the prochiral diester 8 to cause formation of an asymmetric monoacid with at least 98% enantiomeric excess. Reduction of the acid, saponification of the remaining ester, and radical iododecarboxylation gave an iodide that after substitution with silver trifluoroacetate and hydrolysis gave 2.

  DOI：

  10.1021/jo000699r

文献信息

• Chemoenzymatic Synthesis of Isogalactofagomine
  作者：Xifu Liang、Anders Lohse、Mikael Bols

  DOI：10.1021/jo000699r

  日期：2000.11.1

  A new chemoenzymatic synthesis of optically pure isogalactofagomine 2 starting from achiral starting materials is presented. Dimethyl 4-hydroxypyridine-3,5-dicarboxylate (7) was synthesized and converted to the corresponding saturated piperidine 8. Then the key step of the synthesis was carried out: Lipase M catalyzed hydrolysis of the prochiral diester 8 to cause formation of an asymmetric monoacid with at least 98% enantiomeric excess. Reduction of the acid, saponification of the remaining ester, and radical iododecarboxylation gave an iodide that after substitution with silver trifluoroacetate and hydrolysis gave 2.