2,2,2-Trichloro-acetimidic acid (2R,3S,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester | 647021-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,2-Trichloro-acetimidic acid (2R,3S,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester
• CAS: 647021-60-1
• 化学式: C₂₅H₃₂Cl₃NO₄Si
• 分子量: 544.978
• InChiKey: LUONEJMEDKBESZ-BDTNDASRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60.77
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-acetimidic acid (2R,3S,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl ester 在 potassium carbonate 作用下， 以 二苯醚 为溶剂， 以72%的产率得到N-[(2S,3R,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-yl]-2,2,2-trichloro-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
• 作为产物：
  描述：

  2-萘甲醇 在 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 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 2,2,2-Trichloro-acetimidic acid (2R,3S,6S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-(naphthalen-2-ylmethoxy)-3,6-dihydro-2H-pyran-3-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