(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine | 1354826-71-3

• 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,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine
• 英文别名: (2R,3R,4R,5S,6S)-1-benzyl-2-(fluoromethyl)-3,4,5-tris(phenylmethoxy)-6-prop-2-enylpiperidine
• CAS: 1354826-71-3
• 化学式: C₃₇H₄₀FNO₃
• 分子量: 565.728
• InChiKey: DIFSSFWPXLPWLF-RHAMUZCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3R,4R,5R,6S,7S)-7-allyl-1-benzyl-4,5,6-tris(benzyloxy)azepan-3-ol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以63%的产率得到(2S,3S,4R,5R,6R)-2-allyl-1-benzyl-3,4,5-tris(benzyloxy)-6-(fluoromethyl)piperidine
  参考文献：
  名称：

  Access to l- and d-Iminosugar C-Glycosides from a d-gluco-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy

  摘要：

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.

  DOI：

  10.1021/ol203385w

文献信息

• Access to <scp>l</scp>- and <scp>d</scp>-Iminosugar C-Glycosides from a <scp>d</scp>-<i>gluco</i>-Derived 6-Azidolactol Exploiting a Ring Isomerization/Alkylation Strategy
  作者：Martine Mondon、Nathalie Fontelle、Jérôme Désiré、Frédéric Lecornué、Jérôme Guillard、Jérôme Marrot、Yves Blériot

  DOI：10.1021/ol203385w

  日期：2012.2.3

  A flexible synthetic access to six-membered and D-iminosugar C-glycosides is reported starting from the easily available 6-azido-6-deoxy-2,3,4-tri-O-benzyl-D-glucopyranose precursor. This methodology involves a highly diastereoselective tandem ring enlargement/alkylation and a stereocontrolled ring contraction. It allows an efficient synthesis of iminosugar C-glycosides displaying structural diversity at both C-1 and C-6.