2,2,2-Trichloro-N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-yl]-acetamide | 647021-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trichloro-N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS: 647021-55-4
• 化学式: C₁₉H₂₀Cl₃NO₆
• 分子量: 464.73
• InChiKey: KOONMROMRFGFQS-MTSZKFMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108.25
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-yl]-acetamide 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 硝基甲烷 为溶剂， 生成 Acetic acid (2R,4aR,6S,7R,8S,8aS)-6-(naphthalen-2-ylmethoxy)-2-phenyl-7-(2,2,2-trichloro-acetylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620
• 作为产物：
  描述：

  2-萘甲醇 在 盐酸 、 四氧化锇 、 quinuclidine N-oxide 、 三氟化硼乙醚 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二苯醚 、 二氯甲烷 、 水 为溶剂， 反应 73.0h， 生成 2,2,2-Trichloro-N-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-2-(naphthalen-2-ylmethoxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  Trichloro-oxazolines as Activated Donors for Aminosugar Coupling

  摘要：

  [GRAPHICS]Starting from tri-O-acetyl-D-glucal, a combination of the Overman rearrangement and subsequent dihydroxylation produces a range of aminosugars. These can be activated by formation of the corresponding trichloro-oxazolines, which are excellent glycosyl donors as they form disaccharides with good (trans) stereoselectivity under mild conditions. Propagation of these trichloro-oxazolines gave trisaccharides that can then be dehalogenated under a variety of conditions.

  DOI：

  10.1021/ol0359620