(2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine | 849928-69-4

• 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: (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine
• 英文别名: tert-butyl (2S,3R)-2-[(1S,2R)-3-ethoxy-1,2-dihydroxy-3-oxopropyl]-3-phenylmethoxypiperidine-1-carboxylate
• CAS: 849928-69-4
• 化学式: C₂₂H₃₃NO₇
• 分子量: 423.507
• InChiKey: RIKVHMROGBEFJU-AKHDSKFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 18.0h， 以84%的产率得到(1S,2R,8R,8aS)-8-benzyloxy-1,2-dihydroxyhexahydroindolizin-3-one
  参考文献：
  名称：

  General Approach to Glycosidase Inhibitors. Enantioselective Synthesis of Deoxymannojirimycin and Swainsonine

  摘要：

  Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

  DOI：

  10.1021/jo048172s
• 作为产物：
  描述：

  tert-butyl (2S,3R)-3-(benzyloxy)-2-(hydroxymethyl)piperidine-1-carboxylate 在 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 50.0h， 生成 (2S,3R,1'S,2'R)-N-tert-butoxycarbonyl-3-benzyloxy-2-[2'-ethoxycarbonyl-1',2'-dihydroxyethyl]piperidine
  参考文献：
  名称：

  General Approach to Glycosidase Inhibitors. Enantioselective Synthesis of Deoxymannojirimycin and Swainsonine

  摘要：

  Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.

  DOI：

  10.1021/jo048172s

文献信息

• General Approach to Glycosidase Inhibitors. Enantioselective Synthesis of Deoxymannojirimycin and Swainsonine
  作者：Rubén Martín、Caterina Murruzzu、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo048172s

  日期：2005.3.1

  Deoxymannojirimycin (2) and swainsonine (4) have been synthesized from each enantiomer of the same bicyclic carbamate precursor 7. The key intermediate was prepared by a simple and efficient three-step synthesis involving RCM of the diene 8, which in turn is easily accessible in any configuration from enantiomerically enriched 2,3-epoxy-4-penten-1-ol 9.