N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[2,2-dimethylbutanoyl]oxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide

• 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: N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[2,2-dimethylbutanoyl]oxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide
• 英文别名: [(1S,3R,7S,8S,8aR)-8-[(3R,5R)-7-(cyclopropylamino)-3,5-dihydroxy-7-oxoheptyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate
• 化学式: C₂₈H₄₅NO₅
• 分子量: 475.669
• InChiKey: LVWGMISPMGIKKH-XJHKZTBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  95.86
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[2,2-dimethylbutanoyl]oxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide 、 在 sodium hydroxide 、 盐酸 、 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 19.5h， 以97.6%的产率得到(3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-二甲基丁酰氧基)-1,2,6,7,8,8a-六氢-2,6-二甲基-1-萘基]-3,5-二羟基庚酸铵
  参考文献：
  名称：

  A Cost-Efficient Synthesis of Simvastatin via High-Conversion Methylation of an Alkoxide Ester Enolate

  摘要：

  A cost-efficient synthesis of simvastatin (2), starting from mevinolin (lovastatin) (1a) or its precursor mevinolinic acid (1b), is reported. This synthesis involves the use of a new intermediate, lovastatin cyclopropylamide (3), eliminating two chemical steps of protection and deprotection of the open dihydroxy form of (la), Synthesis is based on the high-conversion methylation of an alkoxide ester enolate and involves only four chemical steps. Methylation reaction conditions have been optimized to get >99.5% conversion, Process is economical on large-scale and product (2) is obtained in 85% overall yield.

  DOI：

  10.1021/op990187i
• 作为产物：
  描述：

  洛伐他汀 在 四氢吡咯 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 10.0h， 生成 N-cyclopropyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[2,2-dimethylbutanoyl]oxy-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoic acid amide
  参考文献：
  名称：

  A Cost-Efficient Synthesis of Simvastatin via High-Conversion Methylation of an Alkoxide Ester Enolate

  摘要：

  A cost-efficient synthesis of simvastatin (2), starting from mevinolin (lovastatin) (1a) or its precursor mevinolinic acid (1b), is reported. This synthesis involves the use of a new intermediate, lovastatin cyclopropylamide (3), eliminating two chemical steps of protection and deprotection of the open dihydroxy form of (la), Synthesis is based on the high-conversion methylation of an alkoxide ester enolate and involves only four chemical steps. Methylation reaction conditions have been optimized to get >99.5% conversion, Process is economical on large-scale and product (2) is obtained in 85% overall yield.

  DOI：

  10.1021/op990187i