(3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate | 191854-41-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate
• 英文别名: methyl 2-[(4R,6S)-6-[acetyloxy-(4-methylphenyl)sulfanylmethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• CAS: 191854-41-8
• 化学式: C₁₉H₂₆O₆S
• 分子量: 382.478
• InChiKey: ZLIKLDFIQWUNII-HMZVSMPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate 在 镍 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 瑞舒伐他汀杂质121
  参考文献：
  名称：

  Chiral Sulfoxides in Asymmetric Synthesis: Enantioselective Synthesis of the Lactonic Moiety of (+)-Compactin and (+)-Mevinolin. Application to a Compactin Analog

  摘要：

  The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a beta,delta-diketo sulfoxide easily obtained by the reaction of the trianion of methyl 3,5-dioxohexanoate with (-)-menthyl (S)-p-toluenesulfinate. The main reaction was the two-step stereoselective reduction of beta,delta-diketo sulfoxide without any protective group.

  DOI：

  10.1021/jo00129a018
• 作为产物：
  描述：

  (+)-<5(S),S(R)> methyl 3-oxo-5-hydroxy-6-(p-tolylsulfinyl) hexanoate 在 对甲苯磺酸 sodium tetrahydroborate 、 二乙基甲氧基硼烷 、 sodium acetate 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 17.33h， 生成 (3R,5S)-Methyl 6-acetoxy-syn-3,5-(isopropylidenedioxy)-6-(p-tolylthio)hexanoate
  参考文献：
  名称：

  Chiral Sulfoxides in Asymmetric Synthesis: Enantioselective Synthesis of the Lactonic Moiety of (+)-Compactin and (+)-Mevinolin. Application to a Compactin Analog

  摘要：

  The lactonic part of (+)-compactin and (+)-mevinolin as well as a compactin analogue were synthesized in an enantioselective way from a beta,delta-diketo sulfoxide easily obtained by the reaction of the trianion of methyl 3,5-dioxohexanoate with (-)-menthyl (S)-p-toluenesulfinate. The main reaction was the two-step stereoselective reduction of beta,delta-diketo sulfoxide without any protective group.

  DOI：

  10.1021/jo00129a018