(3S,4S,5R)-N-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-isopropylidene-3-trifluoroacetoxypiperidine

• 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: (3S,4S,5R)-N-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-isopropylidene-3-trifluoroacetoxypiperidine
• 英文别名: tert-butyl (4aR,8S,8aS)-2,2-dimethyl-8-(2,2,2-trifluoroacetyl)oxy-4,4a,5,7,8,8a-hexahydro-[1,3]dioxino[5,4-c]pyridine-6-carboxylate
• 化学式: C₁₆H₂₄F₃NO₆
• 分子量: 383.365
• InChiKey: QSTZTTLHQCMIQU-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 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：
  9

反应信息

• 作为产物：
  描述：

  (3R,4S,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-3-carboxylic acid 在 碘苯二乙酸 、 碘 作用下， 以 四氯化碳 、 乙酸乙酯 为溶剂， 反应 1.33h， 生成 (3S,4S,5R)-N-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-isopropylidene-3-trifluoroacetoxypiperidine
  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.