[(3R,4S)-4-hydroxy-4-methylhex-5-en-3-yl] (2R,3S,5R,6R,8R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2,6,8-trimethyl-9-oxo-5-triethylsilyloxyundec-10-enoate | 1355616-41-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(3R,4S)-4-hydroxy-4-methylhex-5-en-3-yl] (2R,3S,5R,6R,8R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2,6,8-trimethyl-9-oxo-5-triethylsilyloxyundec-10-enoate
• CAS: 1355616-41-9
• 化学式: C₃₄H₆₆O₇Si₂
• 分子量: 643.065
• InChiKey: VSLBSRVXKLTSQW-VXWQITRKSA-N

物化性质

• 沸点：
  615.5±55.0 °C(predicted)
• 密度：
  0.958±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 重原子数：
  43
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(3R,4S)-4-hydroxy-4-methylhex-5-en-3-yl] (2R,3S,5R,6R,8R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2,6,8-trimethyl-9-oxo-5-triethylsilyloxyundec-10-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以60%的产率得到(3R,4S,6R,7R,9R,11E,13S,14R)-4-[tert-butyl(dimethyl)silyl]oxy-14-ethyl-13-hydroxy-7-methoxy-3,7,9,13-tetramethyl-6-triethylsilyloxy-1-oxacyclotetradec-11-ene-2,10-dione
  参考文献：
  名称：

  Desmethyl Macrolides: Synthesis and Evaluation of 4,10-Didesmethyl Telithromycin

  摘要：

  Novel sources of antibiotics are required to keep pace with the inevitable onset of bacterial resistance. Continuing with our macrolide desmethylation strategy as a source of new antibiotics, we report the total synthesis, molecular modeling, and biological evaluation of 4,10-didesmethyl telithromycin (4), a novel desmethyl analogue of the third-generation drug telithromycin (2). Telithromycin is an FDA-approved ketolide antibiotic derived from erythromycin (1). We found 4,10-didesmethyl telithromycin (4) to be four times more active than previously prepared 4,8,10-tridesmethyl congener (3) in MIC assays. While less potent than telithromycin (2), the inclusion of the C-8 methyl group has improved biological activity, suggesting that it plays an important role in antibiotic function.

  DOI：

  10.1021/ml200254h
• 作为产物：
  描述：

  (3R,4R,6R)-7-((tert-butyldimethylsilyl)oxy)-4-methoxy-4,6-dimethyl-3-((triethylsilyl)oxy)heptan-1-ol 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 草酰氯 、 三氟甲磺酸二丁硼 、 四丁基氟化铵 、 双氧水 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 43.5h， 生成 [(3R,4S)-4-hydroxy-4-methylhex-5-en-3-yl] (2R,3S,5R,6R,8R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-2,6,8-trimethyl-9-oxo-5-triethylsilyloxyundec-10-enoate
  参考文献：
  名称：

  Desmethyl Macrolides: Synthesis and Evaluation of 4,10-Didesmethyl Telithromycin

  摘要：

  Novel sources of antibiotics are required to keep pace with the inevitable onset of bacterial resistance. Continuing with our macrolide desmethylation strategy as a source of new antibiotics, we report the total synthesis, molecular modeling, and biological evaluation of 4,10-didesmethyl telithromycin (4), a novel desmethyl analogue of the third-generation drug telithromycin (2). Telithromycin is an FDA-approved ketolide antibiotic derived from erythromycin (1). We found 4,10-didesmethyl telithromycin (4) to be four times more active than previously prepared 4,8,10-tridesmethyl congener (3) in MIC assays. While less potent than telithromycin (2), the inclusion of the C-8 methyl group has improved biological activity, suggesting that it plays an important role in antibiotic function.

  DOI：

  10.1021/ml200254h