(2R,3R,4R,5S)-4-Benzyloxy-2-benzyloxymethyl-1-nonyl-piperidine-3,5-diol | 888323-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R,4R,5S)-4-Benzyloxy-2-benzyloxymethyl-1-nonyl-piperidine-3,5-diol
• 英文别名: (2R,3R,4R,5S)-1-nonyl-4-phenylmethoxy-2-(phenylmethoxymethyl)piperidine-3,5-diol
• CAS: 888323-17-9
• 化学式: C₂₉H₄₃NO₄
• 分子量: 469.665
• InChiKey: IMAXDHJOMKKKAG-VJLHXPKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-4-Benzyloxy-2-benzyloxymethyl-1-nonyl-piperidine-3,5-diol 在 咪唑 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-1-nonyl-piperidin-3-ol
  参考文献：
  名称：

  A stereodivergent approach to 1-deoxynojirimycin, 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives

  摘要：

  A stereodivergent synthesis of N-alkylated 1-deoxygalactoncjirimycin and 1-deoxymannojirimycin derivatives has been achieved from a protected 1-deoxynojirimycin intermediate having two free OH groups tactically positioned at C-2 and C-4. The inversion of configuration of the secondary alcohols was performed by way of a Swern oxidation followed by a highly diastereoselective reduction using NaBH4 or L-Selectride. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.157
• 作为产物：
  描述：

  壬胺 在 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 92.0h， 生成 (2R,3R,4R,5S)-4-Benzyloxy-2-benzyloxymethyl-1-nonyl-piperidine-3,5-diol
  参考文献：
  名称：

  A stereodivergent approach to 1-deoxynojirimycin, 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives

  摘要：

  A stereodivergent synthesis of N-alkylated 1-deoxygalactoncjirimycin and 1-deoxymannojirimycin derivatives has been achieved from a protected 1-deoxynojirimycin intermediate having two free OH groups tactically positioned at C-2 and C-4. The inversion of configuration of the secondary alcohols was performed by way of a Swern oxidation followed by a highly diastereoselective reduction using NaBH4 or L-Selectride. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.02.157

文献信息

• A stereodivergent approach to 1-deoxynojirimycin, 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives
  作者：Charlotte Boucheron、Philippe Compain、Olivier R. Martin

  DOI：10.1016/j.tetlet.2006.02.157

  日期：2006.5

  A stereodivergent synthesis of N-alkylated 1-deoxygalactoncjirimycin and 1-deoxymannojirimycin derivatives has been achieved from a protected 1-deoxynojirimycin intermediate having two free OH groups tactically positioned at C-2 and C-4. The inversion of configuration of the secondary alcohols was performed by way of a Swern oxidation followed by a highly diastereoselective reduction using NaBH4 or L-Selectride. (c) 2006 Elsevier Ltd. All rights reserved.