(1R)-4-[(1E,3E,5Z,7E)-9-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-3,5,5-trimethylcyclohex-3-en-1-ol | 473758-68-8

• 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: (1R)-4-[(1E,3E,5Z,7E)-9-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
• CAS: 473758-68-8
• 化学式: C₃₆H₄₈O₂Si
• 分子量: 540.861
• InChiKey: ZPQJVWZSMZQKFS-IRROPIAKSA-N

物化性质

• 沸点：
  610.8±55.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.07
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R)-4-[(1E,3E,5Z,7E)-9-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-3,5,5-trimethylcyclohex-3-en-1-ol 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 四丁基氟化铵 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.28h， 生成 (3R)-3-[N⁶-biotinyl-N²-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol bromoacetate
  参考文献：
  名称：

  Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

  摘要：

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00667-1
• 作为产物：
  描述：

  (R)-4-[(1E,3E,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-nona-1,3,7-trien-5-ynyl]-3,5,5-trimethyl-cyclohex-3-enol 在 copper diacetate 、 silver nitrate 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以99%的产率得到(1R)-4-[(1E,3E,5Z,7E)-9-[tert-butyl(diphenyl)silyl]oxy-3,7-dimethylnona-1,3,5,7-tetraenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
  参考文献：
  名称：

  Synthesis of biotinylated retinoids for cross-linking and isolation of retinol binding proteins

  摘要：

  The synthesis of (3R)-3-[Boc-Lys(biotinyl)-O]-11-cis-retinol bromoacetate and 3-[Boc-Lys(biotinyl)-0]-all trans-retinol chloroacetate is described. These biotinylated retinoids a-re instrumental in labeling the retinol binding proteins (RBPs) via a nucleophilic displacement of the haloacetate by a residue in the binding site of the protein. The covalently linked biotin will allow for a facile isolation and purification of the protein on a streptavidin column thus rendering the protein ready for a tryptic digest followed by mass spectrometric analysis. The 11-cis retinoid was synthesized via metal reduction of an alkyne intermediate generated from a Homer-Wadsworth-Emmons (HWE) reaction whereas the all-trans was synthesized via two consecutive HWE couplings. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00667-1