(2S,3R,4S,6R)-4-(dimethylamino)-2-(((1R,2R,5R,6S,7R,8S,10R,12R,13R,14R,E)-5-ethyl-1,6,7-trihydroxy-9-(((2-methoxyethoxy)methoxy)imino)-2,6,8,10,12,14-hexamethyl-3-oxo-4,15-dioxabicyclo[10.2.1]pentadecan-13-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate | 214695-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,6R)-4-(dimethylamino)-2-(((1R,2R,5R,6S,7R,8S,10R,12R,13R,14R,E)-5-ethyl-1,6,7-trihydroxy-9-(((2-methoxyethoxy)methoxy)imino)-2,6,8,10,12,14-hexamethyl-3-oxo-4,15-dioxabicyclo[10.2.1]pentadecan-13-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
• CAS: 214695-04-2
• 化学式: C₃₅H₆₂N₂O₁₃
• 分子量: 718.883
• InChiKey: CBUDEYGBXNXPBJ-VPRSKHLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  184.27
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,6R)-4-(dimethylamino)-2-(((1R,2R,5R,6S,7R,8S,10R,12R,13R,14R,E)-5-ethyl-1,6,7-trihydroxy-9-(((2-methoxyethoxy)methoxy)imino)-2,6,8,10,12,14-hexamethyl-3-oxo-4,15-dioxabicyclo[10.2.1]pentadecan-13-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate 在 甲醇 作用下， 反应 24.0h， 以77%的产率得到(1R,2R,5R,6S,7R,8S,9E,10R,12R,13R,14R)-13-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-5-ethyl-1,6,7-trihydroxy-9-(2-methoxyethoxymethoxyimino)-2,6,8,10,12,14-hexamethyl-4,15-dioxabicyclo[10.2.1]pentadecan-3-one
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d
• 作为产物：
  描述：

  5-(3,4,6-trideoxy-2-O-acetyl-3-dimethylamino-β-D-xylo-hexopyranosyloxy)-3,6,11,12-tetrahydroxy-9-(2-methoxyethoxy)methoxyimino-2,4,6,8,10,12-hexamethylpentadecan-13-olide 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以52%的产率得到(2S,3R,4S,6R)-4-(dimethylamino)-2-(((1R,2R,5R,6S,7R,8S,10R,12R,13R,14R,E)-5-ethyl-1,6,7-trihydroxy-9-(((2-methoxyethoxy)methoxy)imino)-2,6,8,10,12,14-hexamethyl-3-oxo-4,15-dioxabicyclo[10.2.1]pentadecan-13-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl acetate
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Ketolides (6-O-Methyl-3-oxoerythromycin Derivatives):  A New Class of Antibacterials Highly Potent Against Macrolide-Resistant and -Susceptible Respiratory Pathogens

  摘要：

  In the search for new antibiotics active against macrolide-resistant pneumococci and Haemophilus influenzae, we synthesized a new class of 3-oxo-6-O-methylerythromycin derivatives, so-called "ketolides". A keto function was introduced in position 3 after removal of L-cladinose, a sugar which has long been thought essential. Further modifications of the macrolactone backbone allowed us to obtain three different series of 9-oxime, 11,12-carbamate, and 11,12-hydrazonocarbamate ketolides. These compounds were found to be very active against penicillin/erythromycin-resistant pneumococci and noninducers of MLS(B) resistance. The 11,12-substituted ketolide 61 (HMR 3004) demonstrated a potent activity against multiresistant pneumococci associated with a well-balanced activity against all bacteria involved in respiratory infections including H. influenzae, Mycoplasma catarrhalis, group A streptococci, and atypical bacteria. In addition HMR 3004 displayed high therapeutic activity in animals infected by all major strains, irrespective of their resistance phenotype.

  DOI：

  10.1021/jm980240d