(3R,4S,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-3-carboxylic acid methyl ester | 309918-22-7

• 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,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-3-carboxylic acid methyl ester
• 英文别名: 6-O-tert-butyl 8-O-methyl (4aR,8R,8aS)-2,2-dimethyl-4,4a,5,7,8,8a-hexahydro-[1,3]dioxino[5,4-c]pyridine-6,8-dicarboxylate
• CAS: 309918-22-7
• 化学式: C₁₆H₂₇NO₆
• 分子量: 329.393
• InChiKey: DGZNXVAZJGBRMV-UTUOFQBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-3-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以87%的产率得到(3R,4S,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-3-carboxylic acid
  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 硼烷四氢呋喃络合物 、 Murcor javanicus lipase M 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 91.0h， 生成 (3R,4S,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-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.