(3R,4R)-4,7-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-methylheptan-1-ol | 1330118-73-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4R)-4,7-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-methylheptan-1-ol
• 英文别名: (3R,4R)-4,7-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methoxy-4-methylheptan-1-ol
• CAS: 1330118-73-4
• 化学式: C₂₁H₄₈O₄Si₂
• 分子量: 420.781
• InChiKey: VXUYGMPWEVCAHN-WIYYLYMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.97
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (3R,4R)-4,7-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-methylheptan-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 生成 (3R,4R)-4,7-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methoxy-4-methylheptanal
  参考文献：
  名称：

  Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin

  摘要：

  Novel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of our efforts that ultimately led to the total synthesis of (-)-4,8,10-tridesmethyl telithromycin (3) wherein methyl groups have been replaced with hydrogens. The synthesis of desmethyl macrolides has emerged as a novel strategy for preparing bioactive antibiotics.

  DOI：

  10.1021/jo201319b
• 作为产物：
  描述：

  tert-butyl-dimethyl-(4-methyl-7-phenylmethoxyhept-4-enoxy)silane 在 2,6-二甲基吡啶 、 AD-Mix-α 、 palladium 10% on activated carbon 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (3R,4R)-4,7-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-methylheptan-1-ol
  参考文献：
  名称：

  Total Synthesis of (−)-4,8,10-Tridesmethyl Telithromycin

  摘要：

  Novel sources of antibiotics are required to address the serious problem of antibiotic resistance. Telithromycin (2) is a third-generation macrolide antibiotic prepared from erythromycin (1) and used clinically since 2004. Herein we report the details of our efforts that ultimately led to the total synthesis of (-)-4,8,10-tridesmethyl telithromycin (3) wherein methyl groups have been replaced with hydrogens. The synthesis of desmethyl macrolides has emerged as a novel strategy for preparing bioactive antibiotics.

  DOI：

  10.1021/jo201319b