4-O-Acetyl-C-2-myristoyl-1,5-anhydro-2,3,6-trideoxy-3-N-trifluoroacetamido-L-arabino-hex-1-enitol | 146579-15-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-O-Acetyl-C-2-myristoyl-1,5-anhydro-2,3,6-trideoxy-3-N-trifluoroacetamido-L-arabino-hex-1-enitol
• CAS: 146579-15-9
• 化学式: C₂₄H₃₈F₃NO₅
• 分子量: 477.565
• InChiKey: ZTCZVRGSRJQGRX-HSQYWUDLSA-N

物化性质

• 沸点：
  541.9±50.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  33.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldimethylsilyl 2,3,6-trideoxy-3-trifluoroacetamido-β-L-arabino-hexopyranoside 、 4-O-Acetyl-C-2-myristoyl-1,5-anhydro-2,3,6-trideoxy-3-N-trifluoroacetamido-L-arabino-hex-1-enitol 在 三氯化铝 作用下， 以56%的产率得到[(2S,3R,4S)-2-methyl-5-tetradecanoyl-4-[(2,2,2-trifluoroacetyl)amino]-3,4-dihydro-2H-pyran-3-yl] tetradecanoate
  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
• 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-myristoyl-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