N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide | 176198-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide
• 英文别名: N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenyloxan-3-yl]acetamide
• CAS: 176198-89-3
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: WNDKVYXZGSESHN-RGDJUOJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.65
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.02
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide 以91%的产率得到Acetic acid (2R,3R,4R,5S,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-phenyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of 2-azido and 2-N-acetylamino-2-deoxy-β-D-C-glycosides from the corresponding lactones

  摘要：

  The reaction of perbenzylated 2-azido-2-deoxy-D-hexono-1,5-lactones with organometallic reagents followed by reduction provides a new stereocontrolled synthesis of 2-azido-2-deoxy-beta-D-C-glycosides, which can be efficiently transformed into 2-N-acetylamino-2-deoxy-beta-D-C-glycosides.

  DOI：

  10.1039/cc9960000347
• 作为产物：
  描述：

  N-((2S,3S,4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-phenyltetrahydro-2H-pyran-3-yl)acetamide 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到N-((2S,3R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenyl-tetrahydro-pyran-3-yl)-acetamide
  参考文献：
  名称：

  Stereocontrolled synthesis of 2-azido and 2-N-acetylamino-2-deoxy-β-D-C-glycosides from the corresponding lactones

  摘要：

  The reaction of perbenzylated 2-azido-2-deoxy-D-hexono-1,5-lactones with organometallic reagents followed by reduction provides a new stereocontrolled synthesis of 2-azido-2-deoxy-beta-D-C-glycosides, which can be efficiently transformed into 2-N-acetylamino-2-deoxy-beta-D-C-glycosides.

  DOI：

  10.1039/cc9960000347