carbonic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethylester 2,5-dioxo-pyrrolidin-1-yl ester | 1233223-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: carbonic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethylester 2,5-dioxo-pyrrolidin-1-yl ester
• CAS: 1233223-70-5
• 化学式: C₁₅H₂₁N₅O₈
• 分子量: 399.36
• InChiKey: NDVALRQSUQSRQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  28.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  173.15
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-(3-aminoprop-1-ynyl)-3'-O-(2-cyanoethyl)-2'-deoxyuridine 、 carbonic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethylester 2,5-dioxo-pyrrolidin-1-yl ester 在 potassium hydrogencarbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以66%的产率得到5-(prop-2-ynyl)carbamic acid 1-{2-[2-(2-azidoethoxy)-ethoxy]ethoxymethyl}-2-cyanoethyl ester-3'-O-(2-cyanoethyl)-2'-desoxyuridine
  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 54.0h， 生成 carbonic acid 1-{2-[2-(2-azidoethoxy)ethoxy]ethoxymethyl}-2-cyanoethylester 2,5-dioxo-pyrrolidin-1-yl 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