(2R,4R,5R)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-7-phenylmethoxy-5-triethylsilyloxyheptan-4-ol | 1355616-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,4R,5R)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-7-phenylmethoxy-5-triethylsilyloxyheptan-4-ol
• CAS: 1355616-35-1
• 化学式: C₂₈H₅₄O₄Si₂
• 分子量: 510.905
• InChiKey: HJUIKSBUQTVZKE-OROMBRFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  34
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R,5R)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-7-phenylmethoxy-5-triethylsilyloxyheptan-4-ol 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 三氟甲磺酸二丁硼 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 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 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 89.0h， 生成
  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：

  在 咪唑 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 (2R,4R,5R)-1-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-7-phenylmethoxy-5-triethylsilyloxyheptan-4-ol
  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