[(2S,3R,4S)-2-methyl-5-tetradecanoyl-4-[(2,2,2-trifluoroacetyl)amino]-3,4-dihydro-2H-pyran-3-yl] tetradecanoate | 146579-18-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(2S,3R,4S)-2-methyl-5-tetradecanoyl-4-[(2,2,2-trifluoroacetyl)amino]-3,4-dihydro-2H-pyran-3-yl] tetradecanoate
• CAS: 146579-18-2
• 化学式: C₃₆H₆₂F₃NO₅
• 分子量: 645.887
• InChiKey: MRIDUTSZTDPFQV-RQBSCEBTSA-N

物化性质

• 沸点：
  668.8±55.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  45
• 可旋转键数：
  28
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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 [(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

文献信息

• One step C-acylation of glycals and 2-deoxy-hexopyranoses at C-2
  作者：Waldemar Priebe、Grzegorz Grynkiewicz、Nouri Neamati

  DOI：10.1016/0040-4039(93)88015-b

  日期：1992.12

  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.