2-(2-(2-((5-(1,3-dioxolan-2-yl)pyridin-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol | 1292309-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-(2-((5-(1,3-dioxolan-2-yl)pyridin-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol
• CAS: 1292309-86-4
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: GMHRJBPOASQGBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  21.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  79.27
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(2-(2-((5-(1,3-dioxolan-2-yl)pyridin-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol 在 4-二甲氨基吡啶 、 Kryptofix222[18F]钾盐 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.17h， 生成 5-(1,3-dioxolan-2-yl)-2-(2-(2-(2-(fluoro-18F)ethoxy)ethoxy)ethoxy)pyridine
  参考文献：
  名称：

  Fluoride-18 radiolabeling of peptides bearing an aminooxy functional group to a prosthetic ligand via an oxime bond

  摘要：

  We have developed a novel F-18 prosthetic ligand named fluoro-PEG-benzaldehyde (FPBA) 1. [F-18]-FPBA 1 is formed in situ from its radiolabeled precursor [F-18]6. Compound 6 is efficiently synthesized in four steps starting from commercially available 6-bromo-3-pyridine carbaldehyde 2. [F-18]-FPBA was evaluated as a prosthetic ligand to radiolabel three cyclic peptides bearing an aminooxy functional group at the N-terminus position. Acetal [F-18] 6 is purified by either solid-phase extraction (SPE) or reverse-phase HPLC with the overall radiochemical yields (RCY) and radiochemical purity (RCP) in very close agreement. The SPE purification process has the advantage of shorter reaction times (71-87 min for entire reaction sequence), while the use of the reverse-phase HPLC purification process allows the use of up to fifty times less of the expensive synthetic peptides (similar to 50 nmol) in the oxime coupling reaction. We have demonstrated an efficient methodology in the production of [F-18]-FPBA 1 and demonstrated its use as a prosthetic ligand for the labeling of peptides possessing an aminooxy functional group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.124
• 作为产物：
  描述：

  2-溴-5-(1,3-二氧杂烷-2-基)吡啶 、 三乙二醇 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以61%的产率得到2-(2-(2-((5-(1,3-dioxolan-2-yl)pyridin-2-yl)oxy)ethoxy)ethoxy)ethan-1-ol
  参考文献：
  名称：

  Fluoride-18 radiolabeling of peptides bearing an aminooxy functional group to a prosthetic ligand via an oxime bond

  摘要：

  We have developed a novel F-18 prosthetic ligand named fluoro-PEG-benzaldehyde (FPBA) 1. [F-18]-FPBA 1 is formed in situ from its radiolabeled precursor [F-18]6. Compound 6 is efficiently synthesized in four steps starting from commercially available 6-bromo-3-pyridine carbaldehyde 2. [F-18]-FPBA was evaluated as a prosthetic ligand to radiolabel three cyclic peptides bearing an aminooxy functional group at the N-terminus position. Acetal [F-18] 6 is purified by either solid-phase extraction (SPE) or reverse-phase HPLC with the overall radiochemical yields (RCY) and radiochemical purity (RCP) in very close agreement. The SPE purification process has the advantage of shorter reaction times (71-87 min for entire reaction sequence), while the use of the reverse-phase HPLC purification process allows the use of up to fifty times less of the expensive synthetic peptides (similar to 50 nmol) in the oxime coupling reaction. We have demonstrated an efficient methodology in the production of [F-18]-FPBA 1 and demonstrated its use as a prosthetic ligand for the labeling of peptides possessing an aminooxy functional group. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.124