6(R)-<2-<3(R)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6,6-trimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one | 158437-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 6(R)-<2-<3(R)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6,6-trimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
• 英文别名: [(1S,6R,7R,8S,8aR)-8-[2-[(2R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-6-oxooxan-2-yl]ethyl]-6-hydroxy-3,3,7-trimethyl-2,4,6,7,8,8a-hexahydro-1H-naphthalen-1-yl] 2,2-dimethylbutanoate
• CAS: 158437-65-1
• 化学式: C₃₂H₅₆O₆Si
• 分子量: 564.879
• InChiKey: YEQWZXCHBUOUJX-MQXIXTHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6(R)-<2-<3(R)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6,6-trimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以53%的产率得到6(R)-<2-<8(S)-((2,2-Dimethylbutyryl)oxy)-2(S),6,6-trimethyl-1,2,6,7,8,8a(R)-hexahydronaphth-1(S)-yl>ethyl>-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of L-669,262, a Potent HMG-CoA Reductase Inhibitor

  摘要：

  Synthesis of L-669,262, isosimvastatin-3-one, has been achieved in seven steps from simvastatin (MK-733) and has been shown to be one of the most potent inhibitors of HMG-CoA reductase found to date. The synthesis of the 6-methyl homolog of simvastatin is also described.

  DOI：

  10.1021/jo00099a030
• 作为产物：
  描述：

  辛伐他汀 在 咪唑 、 aluminum oxide 、 palladium diacetate 、 sodium tetrahydroborate 、 苯基氯化硒 、 cerium(III) chloride 、 copper(I) bromide dimethylsulfide complex 、 偶氮二异丁腈 、 n-Bu₄SnH 、 三氟化硼乙醚 、 双氧水 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 33.58h， 生成 6(R)-<2-<3(R)-Hydroxy-8(S)-((2,2-dimethylbutyryl)oxy)-2(S),6,6-trimethyl-1,2,3,5,6,7,8,8a(R)-octahydronaphth-1(S)-yl>ethyl>-4(R)-((tert-butyldimethylsilyl)oxy)-3,4,5,6-tetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of L-669,262, a Potent HMG-CoA Reductase Inhibitor

  摘要：

  Synthesis of L-669,262, isosimvastatin-3-one, has been achieved in seven steps from simvastatin (MK-733) and has been shown to be one of the most potent inhibitors of HMG-CoA reductase found to date. The synthesis of the 6-methyl homolog of simvastatin is also described.

  DOI：

  10.1021/jo00099a030

文献信息

• Synthesis of L-669,262, a Potent HMG-CoA Reductase Inhibitor
  作者：Gerald E. Stokker

  DOI：10.1021/jo00099a030

  日期：1994.10

  Synthesis of L-669,262, isosimvastatin-3-one, has been achieved in seven steps from simvastatin (MK-733) and has been shown to be one of the most potent inhibitors of HMG-CoA reductase found to date. The synthesis of the 6-methyl homolog of simvastatin is also described.