methyl (2S,3R)-3-tert-butyldimethylsiloxy-2,4-dimethylhex-(4E)-enoate | 1197011-23-6

• 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: methyl (2S,3R)-3-tert-butyldimethylsiloxy-2,4-dimethylhex-(4E)-enoate
• CAS: 1197011-23-6
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: PKVUQEKJAYHDKL-QFEHZMRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-3-tert-butyldimethylsiloxy-2,4-dimethylhex-(4E)-enoate 在 二异丁基氢化铝 、 水 作用下， 以 甲苯 、 甲醇 为溶剂， 反应 12.5h， 以91%的产率得到(2R,3R,4E)-3-(tert-Butyldimethylsiloxy)-2,4-dimethylhex-4-en-1-ol
  参考文献：
  名称：

  Total synthesis of (+)-piericidin A1 and (−)-piericidin B1

  摘要：

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.07.044
• 作为产物：
  描述：

  (E)-(2S,3R)-3-Hydroxy-2,4-dimethyl-hex-4-enoic acid methyl ester 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以86%的产率得到methyl (2S,3R)-3-tert-butyldimethylsiloxy-2,4-dimethylhex-(4E)-enoate
  参考文献：
  名称：

  Total synthesis of (+)-piericidin A1 and (−)-piericidin B1

  摘要：

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.07.044