4-O-Acetyl-C-2-acetyl-1,5-anhydro-2,3,6-trideoxy-3-N-trifluoroacetamido-L-arabino-hex-1-enitol | 146579-13-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-Acetyl-C-2-acetyl-1,5-anhydro-2,3,6-trideoxy-3-N-trifluoroacetamido-L-arabino-hex-1-enitol
• 英文别名: [(2S,3R,4S)-5-acetyl-2-methyl-4-[(2,2,2-trifluoroacetyl)amino]-3,4-dihydro-2H-pyran-3-yl] acetate
• CAS: 146579-13-7
• 化学式: C₁₂H₁₄F₃NO₅
• 分子量: 309.242
• InChiKey: HRWVZXUXRIPPTK-JUWDTYFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-O-acetyl-1-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-trifluoroacetamido-β-L-arabino-hexopyranose 在 三氯化铝 、 乙酸酐 、 zinc(II) chloride 作用下， 生成 4-O-Acetyl-C-2-acetyl-1,5-anhydro-2,3,6-trideoxy-3-N-trifluoroacetamido-L-arabino-hex-1-enitol
  参考文献：
  名称：

  One step C-acylation of glycals and 2-deoxy-hexopyranoses at C-2

  摘要：

  A simple method has been developed for synthesizing previously unknown 2-C-acyl glycals. Direct Friedel-Crafts acylation of glycals with acetyl chloride or acetic anhydride in the presence of AlCl3 or FeCl3 gave 2-C-acetyl-hex-1-enitols in yields often better than 80%-90%. Interestingly, the 2-C-acetyl-hex-1-enitols can also be prepared in a single step from 1-O-acetyl-and 1-O-silyl-2-deoxy-hexopyranoses, and for all reactions excellent yields were observed.

  DOI：

  10.1016/0040-4039(93)88015-b