Diethyl (4S,5S)-4,5-bis<(triethylsilyl)oxy>-(2E,6E)-octadienedioate | 153313-63-4

• 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: Diethyl (4S,5S)-4,5-bis<(triethylsilyl)oxy>-(2E,6E)-octadienedioate
• 英文别名: diethyl (2E,4S,5S,6E)-4,5-bis(triethylsilyloxy)octa-2,6-dienedioate
• CAS: 153313-63-4
• 化学式: C₂₄H₄₆O₆Si₂
• 分子量: 486.797
• InChiKey: VCGUNZQWVWGICC-BPEDCEQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.01
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl (4S,5S)-4,5-bis<(triethylsilyl)oxy>-(2E,6E)-octadienedioate 、 苄胺 以 乙醇 为溶剂， 反应 36.0h， 生成 ((2S,3S,4S,5S)-1-Benzyl-5-ethoxycarbonylmethyl-3,4-bis-triethylsilanyloxy-pyrrolidin-2-yl)-acetic acid ethyl ester 、 ((2S,3S,4S,5R)-1-Benzyl-5-ethoxycarbonylmethyl-3,4-bis-triethylsilanyloxy-pyrrolidin-2-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Conformational diagnosis of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate based on the stereochemical outcomes of representative reactions as compared with those of its 4,5-O-isopropylidene derivatives and on a dichroic exciton chirality method

  摘要：

  In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.

  DOI：

  10.1021/jo00075a024
• 作为产物：
  描述：

  diethyl (-)-(4S,5S)-4,5-O-isopropylidene-4,5-dihydroxy-2,6-octadienedioate 在 吡啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 Diethyl (4S,5S)-4,5-bis<(triethylsilyl)oxy>-(2E,6E)-octadienedioate
  参考文献：
  名称：

  Conformational diagnosis of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate based on the stereochemical outcomes of representative reactions as compared with those of its 4,5-O-isopropylidene derivatives and on a dichroic exciton chirality method

  摘要：

  In order to gain more insight into the conformation of diethyl (4S,5S)-4,5-bis(tert-butyldimethylsiloxy)-2E,6E-octadienedioate (1) experimentally, some appropriate reactions of 1 and its derivative (S,S)-3, which bears isopropylidene protecting groups, have been executed. The stereochemical outcomes of such reactions as the Diels-Alder reaction, osmium tetraoxide-catalyzed hydroxylation, conjugate addition with amines, and cyclopropanation with phosphonium ylides point to a rigid conformation (1A) in which the vicinal TBDMSO groups, the most bulky substituents, are arranged in an anti relationship, and, therefore, the enoate groups are forced to be gauche each other. A dichroic exciton chirality study has also provided clear-cut evidence for this rigid conformation.

  DOI：

  10.1021/jo00075a024