(3R,4S,5R)-N-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-3-iodo-4,5'-isopropylidene-piperidine | 309918-26-1

• 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-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-3-iodo-4,5'-isopropylidene-piperidine
• 英文别名: tert-butyl (4aR,8R,8aS)-8-iodo-2,2-dimethyl-4,4a,5,7,8,8a-hexahydro-[1,3]dioxino[5,4-c]pyridine-6-carboxylate
• CAS: 309918-26-1
• 化学式: C₁₄H₂₄INO₄
• 分子量: 397.253
• InChiKey: KOJNFWJJAQRVSU-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R)-N-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-3-iodo-4,5'-isopropylidene-piperidine 以 水 、 乙酸乙酯 为溶剂， 反应 0.41h， 生成 (3R,4S,5R)-3,4-dihydroxy-5-hydroxymethylpiperidine hydrotrifluoroacetate
  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 lithium hydroxide 、 硼烷四氢呋喃络合物 、 碘苯二乙酸 、 Murcor javanicus lipase M 、 碘 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 四氯化碳 、 phosphate buffer 、 水 为溶剂， 反应 96.0h， 生成 (3R,4S,5R)-N-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-3-iodo-4,5'-isopropylidene-piperidine
  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