5-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-2,3-O-isopropylidene-D-allo-hexofuranone | 149903-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-2,3-O-isopropylidene-D-allo-hexofuranone
• 英文别名: (3aR,6S,6aR)-6-[(1S)-1-[tert-butyl(dimethyl)silyl]oxy-2,2,2-trifluoroethyl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 149903-06-0
• 化学式: C₁₅H₂₅F₃O₅Si
• 分子量: 370.441
• InChiKey: PZNKDNHTRFCAMK-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-2,3-O-isopropylidene-D-allo-hexofuranone 在 potassium tert-butylate 、 二异丁基氢化铝 作用下， 生成 4-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-2,3-O-isopropylidene-D-allo-hexopyranose
  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'-(1'-acetoxy-2',2',2'-trifluoroethyl)>-5-(trimethylsilyl)furan 在 18-冠醚-6 咪唑 、 potassium permanganate 、 溶剂黄146 作用下， 生成 5-O-(tert-butyldimethylsilyl)-6-deoxy-6,6,6-trifluoro-2,3-O-isopropylidene-D-allo-hexofuranone
  参考文献：
  名称：

  Preparation of 6-deoxy-6,6,6-trifluoro-D-mannose and D-allose from enzymatically resolved 2-butenolides

  摘要：

  Both 6-deoxy-6,6,6-trifluoro-D-mannose and D-allose, possessing a diastereomeric relationship, were conveniently prepared from trifluorinated 2-butenolides, which was prepared via the enzymatic resolution with high efficiency.

  DOI：

  10.1016/s0957-4166(00)80154-8