3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose | 134311-53-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (1R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethanol
• CAS: 134311-53-8
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: LILCKDAOVCWFFG-KAMPLNKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 硫酸 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 89.0h， 生成 (3aR,5R,6R,7S,7aR)-5-methyl-7-prop-2-enoxyspiro[5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2,1'-cyclopentane]-6-ol
  参考文献：
  名称：

  Smith III, Amos B.; Rivero, Ralph A.; Hale, Karl J., Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2092 - 2112

  摘要：

  DOI：
• 作为产物：
  描述：

  双丙酮葡萄糖 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 potassium hydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 125.08h， 生成 3-O-allyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Smith III, Amos B.; Rivero, Ralph A.; Hale, Karl J., Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2092 - 2112

  摘要：

  DOI：

文献信息

• Exploring the Optimal Site for Modifications of Pyranmycins with the Extended Arm Approach
  作者：Jie Li、Jinhua Wang、Yu Hui、Cheng-Wei Tom Chang

  DOI：10.1021/ol027288c

  日期：2003.2.1

  [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.
• 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.