Acetic acid (3aR,4R,5S,7aS)-7a-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-ylmethyl ester | 165336-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: Acetic acid (3aR,4R,5S,7aS)-7a-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-ylmethyl ester
• 英文别名: [(3aR,4R,5S,7aS)-7a-[tert-butyl(dimethyl)silyl]oxy-5-hydroxy-4-methyl-1-oxo-3a,5-dihydro-3H-2-benzofuran-4-yl]methyl acetate
• CAS: 165336-15-2
• 化学式: C₁₈H₃₀O₆Si
• 分子量: 370.518
• InChiKey: COWULIJDIZELJO-USJZOSNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  Acetic acid (3aR,4R,5S,7aS)-7a-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-ylmethyl ester 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以100%的产率得到(3aR,4R,5S,7aS)-7a-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one
  参考文献：
  名称：

  Enzymatic resolution of a key stereochemical intermediate for the synthesis of (−)-taxol

  摘要：

  The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase Bin isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.

  DOI：

  10.1016/0040-4039(95)00523-f
• 作为产物：
  描述：

  乙酸异丙烯酯 、 (3aR,4R,5S,7aS)-7a-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one 在 SP-435 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以93%的产率得到Acetic acid (3aR,4R,5S,7aS)-7a-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-ylmethyl ester
  参考文献：
  名称：

  Enzymatic resolution of a key stereochemical intermediate for the synthesis of (−)-taxol

  摘要：

  The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase Bin isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.

  DOI：

  10.1016/0040-4039(95)00523-f