(3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-1-nonyl-piperidin-3-ol | 888323-22-6

• 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: (3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-1-nonyl-piperidin-3-ol
• 英文别名: (3R,4R,5R,6R)-1-nonyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)piperidin-3-ol
• CAS: 888323-22-6
• 化学式: C₃₆H₄₉NO₄
• 分子量: 559.789
• InChiKey: INCZFAUOPYBGDF-MGXDLYCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-1-nonyl-piperidin-3-ol 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到N-nonyl 1-deoxymannojirimycin
  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 咪唑 、 草酰氯 、 四丁基氟化铵 、 L-Selectride 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 132.0h， 生成 (3R,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

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.