acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-17-methoxymethoxyimino-2,6,8,10,16,18-hexamethyl-13-methylene-5-oxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester | 625390-05-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-17-methoxymethoxyimino-2,6,8,10,16,18-hexamethyl-13-methylene-5-oxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS: 625390-05-8
• 化学式: C₃₇H₆₄N₂O₁₂
• 分子量: 728.921
• InChiKey: JNHWHZUIYQWLJP-OXRSDXNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  51.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  164.04
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-17-methoxymethoxyimino-2,6,8,10,16,18-hexamethyl-13-methylene-5-oxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester 在 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1R,2R,3R,6R,8R,9R,10R,16S,17E,18R)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2-hydroxy-17-(methoxymethoxyimino)-2,6,8,10,16,18-hexamethyl-13-methylidene-4,11,15-trioxabicyclo[8.5.4]nonadecane-5,7-dione
  参考文献：
  名称：

  Synthesis of Novel 6,11-O-Bridged Bicyclic Ketolides via a Palladium-Catalyzed Bis-allylation

  摘要：

  A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-pi-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance.

  DOI：

  10.1021/ol048336r
• 作为产物：
  描述：

  erythromycin A 9-(E)-oxime 在 盐酸 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium hydride 、 三乙胺 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 acetic acid 4-dimethylamino-2-(3-ethyl-2,7-dihydroxy-17-methoxymethoxyimino-2,6,8,10,16,18-hexamethyl-13-methylene-5-oxo-4,11,15-trioxa-bicyclo[8.5.4]nonadec-9-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of Novel 6,11-O-Bridged Bicyclic Ketolides via a Palladium-Catalyzed Bis-allylation

  摘要：

  A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-pi-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance.

  DOI：

  10.1021/ol048336r