(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid | 205647-16-1

• 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)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid
• 英文别名: (3R)-3-[tert-butyl(dimethyl)silyl]oxy-6-methylsulfinyl-5-oxohexanoic acid
• CAS: 205647-16-1
• 化学式: C₁₃H₂₆O₅SSi
• 分子量: 322.498
• InChiKey: AQLWLPUYOCNKQK-AMIJKRQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.92h， 以74%的产率得到(4R)-[(tert-butyldimethylsilyl)oxy]-6-[(methanesulfinyl)methylene]tetrahydropyran-2-one
  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：

  (3S)-3-[[叔丁基二甲基硅烷基]氧基]-戊烷二酸 1-甲基酯 、 二甲基亚砜 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.59h， 以100%的产率得到(3R)-[(tert-butyldimethylsilyl)oxy]-6-(methanesulfinyl)-5-oxohexanoic acid
  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

文献信息

• Optical Resolution of 3-(Silyloxy)glutaric Acid Half Esters and Their Utilization for Enantioconvergent Synthesis of a HMG-CoA Reductase Inhibitor
  作者：Toshiro Konoike、Tetsuo Okada、Yoshitaka Araki

  DOI：10.1021/jo9722156

  日期：1998.5.1

  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.