3-O-(2-azidoethyl)-2,4-di-O-acetyl-6-deoxy-D-glucopyranosyl trichloroacetimidate | 502621-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2-azidoethyl)-2,4-di-O-acetyl-6-deoxy-D-glucopyranosyl trichloroacetimidate
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-4-(2-azidoethoxy)-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] acetate
• CAS: 502621-21-8
• 化学式: C₁₄H₁₉Cl₃N₄O₇
• 分子量: 461.686
• InChiKey: JGMSUZIKFGOTMJ-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-azidoethyl)-2,4-di-O-acetyl-6-deoxy-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
  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：

  3-O-(2-hydroxyethyl)-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 sodium azide 、 乙酸肼 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-O-(2-azidoethyl)-2,4-di-O-acetyl-6-deoxy-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

文献信息

• Application of the Synthetic Aminosugars for Glycodiversification:  Synthesis and Antimicrobial Studies of Pyranmycin
  作者：Bryan Elchert、Jie Li、Jinhua Wang、Yu Hui、Ravi Rai、Roger Ptak、Priscilla Ward、Jon Y. Takemoto、Mekki Bensaci、Cheng-Wei Tom Chang

  DOI：10.1021/jo035290r

  日期：2004.3.1

  A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.