prop-2-ynylcarbamic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethyl ester | 1233223-68-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: prop-2-ynylcarbamic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethyl ester
• CAS: 1233223-68-1
• 化学式: C₁₄H₂₁N₅O₅
• 分子量: 339.351
• InChiKey: FPOMPBGKZPEOBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  24.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138.57
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  碘苯 、 prop-2-ynylcarbamic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethyl ester 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以92%的产率得到(3-phenylprop-2-ynyl)carbamic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethyl ester
  参考文献：
  名称：

  Fluorescent Labeling of (Oligo)Nucleotides by a New Fluoride Cleavable Linker Capable of Versatile Attachment Modes

  摘要：

  The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.

  DOI：

  10.1021/bc900542f
• 作为产物：
  描述：

  2-[2-(2-叠氮基乙氧基)乙氧基]乙醇 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 57.0h， 生成 prop-2-ynylcarbamic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethyl ester
  参考文献：
  名称：

  Fluorescent Labeling of (Oligo)Nucleotides by a New Fluoride Cleavable Linker Capable of Versatile Attachment Modes

  摘要：

  The development of a fluoride cleavable linker 1 for reversibly labeling (oligo)nucleotides is described here. The linker allows different ways of chemical attachment of a reporter molecule, for example, click chemistry or amide formation. The versatile attachment modes of labels are demonstrated by derivatizations with pyrene and fluorescein. Besides the synthesis of the new linker, we also show the derivatization of iodobenzene as a model compound and a nucleoside to demonstrate the applicability. Further, cleavability studies in solution and on a solid-supported oligonucleotide are shown. The linker can be applied in the synthesis of reversible terminators, useful for new DNA sequencing technologies like cyclic reversibly terminating (CRT) sequencing.

  DOI：

  10.1021/bc900542f