(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester | 205647-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester
• 英文别名: methyl (3R)-3-[tert-butyl(dimethyl)silyl]oxy-7-[4-(4-fluorophenyl)-5-methyl-2-propan-2-yl-1H-pyrrol-3-yl]-6-methylsulfinyl-5-oxoheptanoate
• CAS: 205647-21-8
• 化学式: C₂₉H₄₄FNO₅SSi
• 分子量: 565.822
• InChiKey: YRKFMCSFOIKCHA-ZYAQWATASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester 以 甲苯 为溶剂， 反应 1.0h， 以91%的产率得到(3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-5-oxo-6-heptenoic acid methyl ester
  参考文献：
  名称：

  Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor

  摘要：

  Useful chiral synthons, (3R)- and (3S)-[(tert-butyldimethylsilyl)oxy]penta acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from(S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and(S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.

  DOI：

  10.1021/jo9722156
• 作为产物：
  描述：

  [[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]methyl]dimethylamine 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 2.75h， 生成 (3R)-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-2-isopropyl-5-methyl-1H-pyrrol-3-yl]-6-(methanesulfinyl)-5-oxoheptanoic acid methyl ester
  参考文献：
  名称：

  Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor

  摘要：

  Useful chiral synthons, (3R)- and (3S)-[(tert-butyldimethylsilyl)oxy]penta acid monomethyl ester, (R)-1 and (S)-1, were obtained by optical resolution of a racemic mixture of 1. Sulfoxide 8 has been developed from(S)-1 as a new building block for preparing HMG-CoA reductase inhibitors. Two alternate chiral synthons 2 and 8, synthesized from (R)-1 and(S)-1, respectively, were employed for enantioconvergent synthesis of potent inhibitor 15 containing a pyrrole moiety.

  DOI：

  10.1021/jo9722156