(4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene | 1197011-30-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene
• 英文别名: [(2E,4R,5R,6E)-8-(benzenesulfonyl)-3,5,7-trimethylocta-2,6-dien-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1197011-30-5
• 化学式: C₂₃H₃₈O₃SSi
• 分子量: 422.704
• InChiKey: RWXGQVALGGQNOX-ZXFMBSQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methylpent-(2E)-enyl]-pyridine 、 (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 生成 2-[(2E,5E,7E,11E)-(9R,10R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,7,9,11-tetramethyl-trideca-2,5,7,11-tetraenyl]-5,6-dimethoxy-3-methyl-pyridin-4-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：

  (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfanyl-octa-(2E,6E)-diene 在 hexaammonium heptamolybdate tetrahydrate 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 以57%的产率得到(4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene
  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

文献信息

• Total synthesis of (+)-piericidin A1 and (−)-piericidin B1
  作者：Ryosuke Kikuchi、Mikio Fujii、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2009.07.044

  日期：2009.9

  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.