(2S,3R,4R,6R)-6-ethyl-2-(hydroxymethyl)piperidine-3,4-diol | 1345017-62-0

• 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,4R,6R)-6-ethyl-2-(hydroxymethyl)piperidine-3,4-diol
• 英文别名: 5-epi-ethylfagomine
• CAS: 1345017-62-0
• 化学式: C₈H₁₇NO₃
• 分子量: 175.228
• InChiKey: QWEWPBRDYZVGBR-ULAWRXDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3aR,4S,6R,7aR)-tert-butyl-4-((tert-butyldiphenylsilyloxy)methyl)-6-ethyl-2,2-dimethyltetrahydro-[1,3]dioxolo[4,5-c]pyridine-5(6H)-carboxylate 在 水 、 三氟乙酸 、 氨 作用下， 以 水 为溶剂， 反应 12.0h， 以70%的产率得到(2S,3R,4R,6R)-6-ethyl-2-(hydroxymethyl)piperidine-3,4-diol
  参考文献：
  名称：

  [2,3]-Wittig rearrangement approach to iminosugar C-glycosides: 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine and formal synthesis of indolizidine 167B and 209D

  摘要：

  A new strategy for the synthesis of 1,2-dideoxy iminosugar C-glycosides and indolizidines involving highly stereoselective [2,3]-Wittig rearrangement from Garner aldehyde has been developed. This rearrangement yielded an optically pure, highly functionalized key intermediate, which has been further utilized for the synthesis of 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine, and 5-hydroxymethyl indolizidine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.08.084

文献信息

• [2,3]-Wittig rearrangement approach to iminosugar C-glycosides: 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine and formal synthesis of indolizidine 167B and 209D
  作者：B. Chandrasekhar、J. Prasada Rao、B. Venkateswara Rao、P. Naresh

  DOI：10.1016/j.tetlet.2011.08.084

  日期：2011.11

  A new strategy for the synthesis of 1,2-dideoxy iminosugar C-glycosides and indolizidines involving highly stereoselective [2,3]-Wittig rearrangement from Garner aldehyde has been developed. This rearrangement yielded an optically pure, highly functionalized key intermediate, which has been further utilized for the synthesis of 5-epi-ethylfagomine, 2-epi-5-deoxyadenophorine, and 5-hydroxymethyl indolizidine. (C) 2011 Elsevier Ltd. All rights reserved.