methyl 2,3-O-diacetyl-4-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-D-manno-hexopyranoside | 149903-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-diacetyl-4-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-D-manno-hexopyranoside
• 英文别名: [(3S,4R,5S,6S)-3-acetyloxy-5-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-6-(trifluoromethyl)oxan-4-yl] acetate
• CAS: 149903-21-9
• 化学式: C₁₇H₂₉F₃O₇Si
• 分子量: 430.494
• InChiKey: NYTPZFYPSBWPTA-GBUDGIQGSA-N

物化性质

• 沸点：
  382.7±42.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-diacetyl-4-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-D-manno-hexopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到methyl 2,3-O-diacetyl-6-deoxy-6,6,6-trifluoro-D-manno-hexopyranoside
  参考文献：
  名称：

  Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group

  摘要：

  Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6. Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity. Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by the utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

  DOI：

  10.1021/jo00068a033
• 作为产物：
  描述：

  2-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-5-(trimethylsilyl)furan 在 吡啶 、 咪唑 、 potassium permanganate 、 18-冠醚-6 、 水 、 二异丁基氢化铝 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 12.0h， 生成 methyl 2,3-O-diacetyl-4-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-D-manno-hexopyranoside
  参考文献：
  名称：

  Development of a novel pathway to access 6-deoxy-6,6,6-trifluoro sugars via 1,2-migration of a tert-butyldimethylsilyl group

  摘要：

  Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6. Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity. Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by the utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

  DOI：

  10.1021/jo00068a033