triethylamine (2R,3S,5R)-2-(azidomethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-chlorophenyl) phosphate | 1426257-43-3

• 分子结构分类: 有机化合物
• 英文名称: triethylamine (2R,3S,5R)-2-(azidomethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-chlorophenyl) phosphate
• CAS: 1426257-43-3
• 化学式: C₆H₁₅N*C₁₆H₁₇ClN₅O₇P
• 分子量: 558.959
• InChiKey: BOTPVPFRVQJUQC-SOIKFHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  171.85
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-phenylspiro[cyclopropane-1,3'-indolin]-2'-one 、 triethylamine (2R,3S,5R)-2-(azidomethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-chlorophenyl) phosphate 在 吡啶 、 苯甲基-2-磺酰三硝基三氮唑 、 N-甲基咪唑 作用下， 反应 1.08h， 生成
  参考文献：
  名称：

  Two-Step Synthesis of a 5′-Azidothymidine Building Block for the Assembly of Oligonucleotides for Triazole-Forming Ligations

  摘要：

  A two-step synthesis converting thymidine into a phosphotriester building block of 5'-azido-5'-deoxythymidine in 60% overall yield is presented. The building block was used to assemble an oligonucleotide with an azido group at its 5'-terminus, which underwent ligation-cycloaddition, producing a strand with PCR-compatible linkage in high yield.

  DOI：

  10.1055/s-0032-1317605
• 作为产物：
  描述：

  三乙胺 、 5-叠氮基-5-脱氧胸腺嘧啶脱氧核苷 、 2-氯苯基二氯膦 在 1H-1,2,4-三唑 、 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 以77%的产率得到triethylamine (2R,3S,5R)-2-(azidomethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-chlorophenyl) phosphate
  参考文献：
  名称：

  Two-Step Synthesis of a 5′-Azidothymidine Building Block for the Assembly of Oligonucleotides for Triazole-Forming Ligations

  摘要：

  A two-step synthesis converting thymidine into a phosphotriester building block of 5'-azido-5'-deoxythymidine in 60% overall yield is presented. The building block was used to assemble an oligonucleotide with an azido group at its 5'-terminus, which underwent ligation-cycloaddition, producing a strand with PCR-compatible linkage in high yield.

  DOI：

  10.1055/s-0032-1317605