pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite | 1243167-02-3

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite
• 英文别名: N-[(2-methylpropan-2-yl)oxy-pent-4-ynoxyphosphanyl]-N-propan-2-ylpropan-2-amine
• CAS: 1243167-02-3
• 化学式: C₁₅H₃₀NO₂P
• 分子量: 287.382
• InChiKey: OQMADCXTUHJFJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-戊炔-1-醇 、 叔丁基四异丙基磷酸二阿米迪特 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite
  参考文献：
  名称：

  5′-Bis-conjugation of Oligonucleotides by Amidative Oxidation and Click Chemistry

  摘要：

  A pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite was coupled at the 5'-end of oligonucleotides to give a phosphite triester linkage, which forms an H-phosphonate diester linkage during treatment with dichloroacetic acid. Then an amidative oxidation with CCl(4) in the presence of an amine and a 1,3-dipolar cycloaddition with an azide under copper(1) catalysis afforded the bis-conjugated oligonucleotides with high efficiency. The introduction of a bromoalkyl group as a precursor of azidoalkyl by amidative oxidation allowed the performance of two selective 1,3-dipolar cycloadditions.

  DOI：

  10.1021/jo101134z

文献信息

• 5′-Bis-conjugation of Oligonucleotides by Amidative Oxidation and Click Chemistry
  作者：Albert Meyer、Gwladys Pourceau、Jean-Jacques Vasseur、François Morvan

  DOI：10.1021/jo101134z

  日期：2010.10.1

  A pent-4-ynyl tert-butyl N,N-diisopropyl phosphoramidite was coupled at the 5'-end of oligonucleotides to give a phosphite triester linkage, which forms an H-phosphonate diester linkage during treatment with dichloroacetic acid. Then an amidative oxidation with CCl(4) in the presence of an amine and a 1,3-dipolar cycloaddition with an azide under copper(1) catalysis afforded the bis-conjugated oligonucleotides with high efficiency. The introduction of a bromoalkyl group as a precursor of azidoalkyl by amidative oxidation allowed the performance of two selective 1,3-dipolar cycloadditions.