[(4S,5R,6S)-5-acetyloxy-6-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl] acetate | 121958-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(4S,5R,6S)-5-acetyloxy-6-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl] acetate
• CAS: 121958-77-8
• 化学式: C₁₂H₁₆F₃NO₆
• 分子量: 327.257
• InChiKey: BDDRRYOOBAMSHR-FIEGVUJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(4S,5R,6S)-5-acetyloxy-6-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl] acetate 在 三氯化铝 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
• 作为产物：
  描述：

  4-O-acetyl-1-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-trifluoroacetamido-β-L-arabino-hexopyranose 、 溶剂黄146 在 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 、 [(4S,5R,6S)-5-acetyloxy-6-methyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl] acetate
  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.