N-benzyl-(3S,4S,5S,6S)-5-benzoyloxy-4-benzyloxy-3-hydroxy-6-N-benzylpiperidine-2-one | 163628-05-5

• 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: N-benzyl-(3S,4S,5S,6S)-5-benzoyloxy-4-benzyloxy-3-hydroxy-6-N-benzylpiperidine-2-one
• 英文别名: [(2S,3S,4S,5S)-1-benzyl-2-(benzylamino)-5-hydroxy-6-oxo-4-phenylmethoxypiperidin-3-yl] benzoate
• CAS: 163628-05-5
• 化学式: C₃₃H₃₂N₂O₅
• 分子量: 536.627
• InChiKey: SFNJDICNHYRVCD-MBEDZMRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyl-(3S,4S,5S,6S)-5-benzoyloxy-4-benzyloxy-3-hydroxy-6-N-benzylpiperidine-2-one 在 sodium tetrahydroborate 、 聚合甲醛 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以100%的产率得到N-benzyl-(3S,4S,5R)-3-benzoyloxy-4-benzyloxy-5-hydroxypiperidine
  参考文献：
  名称：

  Synthesis of Polyhydroxylated 6-N-Benzylpiperidin-2-Ones. A Novel Access to 1, 5-Dideoxy-1, 5-imino-D-xylitol

  摘要：

  The synthesis of polyhydroxylated 6-N-benzylpiperidin-2-ones is described from the corresponding N-benzylaminoglycoside. These compounds are easily reduced to the differently protected 1,5-dideoxy-1,5-imino-D-xylitol.

  DOI：

  10.1080/00397919508012674
• 作为产物：
  描述：

  methyl (N-benzyl-2-O-benzoyl-3-O-benzyl-α,β-D-xylofuranosylamine) uronate 、 苄胺 在 三甲基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成 N-benzyl-(3S,4S,5S,6R)-5-benzoyloxy-4-benzyloxy-3-hydroxy-6-N-benzylpiperidine-2-one 、 N-benzyl-(3S,4S,5S,6S)-5-benzoyloxy-4-benzyloxy-3-hydroxy-6-N-benzylpiperidine-2-one
  参考文献：
  名称：

  Synthesis of Polyhydroxylated 6-N-Benzylpiperidin-2-Ones. A Novel Access to 1, 5-Dideoxy-1, 5-imino-D-xylitol

  摘要：

  The synthesis of polyhydroxylated 6-N-benzylpiperidin-2-ones is described from the corresponding N-benzylaminoglycoside. These compounds are easily reduced to the differently protected 1,5-dideoxy-1,5-imino-D-xylitol.

  DOI：

  10.1080/00397919508012674

文献信息

• Synthesis of Polyhydroxylated 6-<i>N</i>-Benzylpiperidin-2-Ones. A Novel Access to 1, 5-Dideoxy-1, 5-imino-D-xylitol
  作者：Francęois-Didier Boyer、Ange Pancrazi、Jean-Yves Lallemand

  DOI：10.1080/00397919508012674

  日期：1995.4

  The synthesis of polyhydroxylated 6-N-benzylpiperidin-2-ones is described from the corresponding N-benzylaminoglycoside. These compounds are easily reduced to the differently protected 1,5-dideoxy-1,5-imino-D-xylitol.