(2R,3R,4S,5S)-N(1)-benzyl-2-(hydroxymethyl)-3-benzyloxy-4,5-dihydroxypiperidine | 1429413-10-4

• 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: (2R,3R,4S,5S)-N(1)-benzyl-2-(hydroxymethyl)-3-benzyloxy-4,5-dihydroxypiperidine
• 英文别名: (3S,4S,5R,6R)-1-benzyl-6-(hydroxymethyl)-5-phenylmethoxypiperidine-3,4-diol
• CAS: 1429413-10-4
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: KVAJXJHZGQOCAK-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S)-N(1)-benzyl-2-(hydroxymethyl)-3-benzyloxy-4,5-dihydroxypiperidine 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 48.0h， 以83%的产率得到(2R,3R,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach

  摘要：

  The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

  DOI：

  10.1021/ol400735z
• 作为产物：
  描述：

  (2R,3R,4S,5S)-N(1)-benzyl-2-[(triisopropylsilyloxy)methyl]-3-benzyloxy-4,5-dihydroxypiperidine 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 生成 (2R,3R,4S,5S)-N(1)-benzyl-2-(hydroxymethyl)-3-benzyloxy-4,5-dihydroxypiperidine
  参考文献：
  名称：

  Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach

  摘要：

  The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.

  DOI：

  10.1021/ol400735z

文献信息

• Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach
  作者：Stephen G. Davies、Aude L. A. Figuccia、Ai M. Fletcher、Paul M. Roberts、James E. Thomson

  DOI：10.1021/ol400735z

  日期：2013.4.19

  The asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.