3-O-(2-acetoxyethyl)-4-azido-2-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate | 502621-14-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2-acetoxyethyl)-4-azido-2-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate
• 英文别名: 2-[(2R,3R,4S,5R,6R)-5-acetyloxy-3-azido-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl]oxyethyl acetate
• CAS: 502621-14-9
• 化学式: C₁₄H₁₉Cl₃N₄O₇
• 分子量: 461.686
• InChiKey: UILAGBFIVCTNFP-UJDFUTJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-O-(2-acetoxyethyl)-4-azido-2-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 (2R,3S,4R,5R,6R)-5-Amino-2-aminomethyl-6-{(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R,6R)-5-amino-3-hydroxy-4-(2-hydroxy-ethoxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-hydroxy-cyclohexyloxy}-tetrahydro-pyran-3,4-diol; compound with acetic acid
  参考文献：
  名称：

  Exploring the Optimal Site for Modifications of Pyranmycins with the Extended Arm Approach

  摘要：

  [GRAPHICS]Continuing from the syntheses and the antibacterial studies of a library of pyranmycins, we further probed the proximity around ring III of pyranmycin by introducing an "extended arm" that has hydroxyethyl or aminoethyl groups at the O-2", O-3", or O-4" positions. The results from the antibacterial studies reveal the optimal structural motif is the attachment of an extended arm with a terminal hydroxyl group at the O-3" position.

  DOI：

  10.1021/ol027288c
• 作为产物：
  描述：

  acetyl 3-O-(2-acetoxyethyl)-4-azido-2-O-acetyl-4,6-dideoxy-α-D-glucopyranoside 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-O-(2-acetoxyethyl)-4-azido-2-O-acetyl-4,6-dideoxy-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Exploring the Optimal Site for Modifications of Pyranmycins with the Extended Arm Approach

  摘要：

  [GRAPHICS]Continuing from the syntheses and the antibacterial studies of a library of pyranmycins, we further probed the proximity around ring III of pyranmycin by introducing an "extended arm" that has hydroxyethyl or aminoethyl groups at the O-2", O-3", or O-4" positions. The results from the antibacterial studies reveal the optimal structural motif is the attachment of an extended arm with a terminal hydroxyl group at the O-3" position.

  DOI：

  10.1021/ol027288c