(4R)-4-benzyl-3-[(2R,3S,5R,6R,8R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methoxy-2,6,8-trimethyl-5-triethylsilyloxynonanoyl]-1,3-oxazolidin-2-one | 1355616-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-4-benzyl-3-[(2R,3S,5R,6R,8R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methoxy-2,6,8-trimethyl-5-triethylsilyloxynonanoyl]-1,3-oxazolidin-2-one
• CAS: 1355616-38-4
• 化学式: C₄₁H₇₇NO₇Si₃
• 分子量: 780.321
• InChiKey: VCSOFYHMWVVMKF-VDUMYCOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.84
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(2R,3S,5R,6R,8R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methoxy-2,6,8-trimethyl-5-triethylsilyloxynonanoyl]-1,3-oxazolidin-2-one 在 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以2.28 g的产率得到(2R,3S,5R,6R,8R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methoxy-2,6,8-trimethyl-5-triethylsilyloxynonanoic acid
  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：

  tert-butyl-[(2R,4R,5R)-4-methoxy-2,4-dimethyl-7-phenylmethoxy-5-triethylsilyloxyheptoxy]-dimethylsilane 在 2,6-二甲基吡啶 、 草酰氯 、 三氟甲磺酸二丁硼 、 palladium 10% on activated carbon 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4R)-4-benzyl-3-[(2R,3S,5R,6R,8R)-3,9-bis[[tert-butyl(dimethyl)silyl]oxy]-6-methoxy-2,6,8-trimethyl-5-triethylsilyloxynonanoyl]-1,3-oxazolidin-2-one
  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