| 473758-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• CAS: 473758-69-9
• 化学式: C₅₇H₈₂N₄O₇SSi
• 分子量: 995.452
• InChiKey: KLBMGINYYFRLNL-NQHAQQHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.52
• 重原子数：
  70.0
• 可旋转键数：
  22.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  144.09
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到3-[N6-biotinyl-N2-(tert-butoxycarbonyl)-L-lysyloxy]-11-cis-retinol
  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：

  (3R)-3-tert-butyldimethylsilyloxy-β-ionone 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 copper(l) iodide 、 正丁基锂 、 copper diacetate 、 四丁基氟化铵 、 silver nitrate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 异丙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成
  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