methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 3'-(2-cyanoethyl diisopropylphosphoramidite) | 289712-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 3'-(2-cyanoethyl diisopropylphosphoramidite)
• 英文别名: methyl 3-[5-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyoxolan-2-yl]-2,4-dioxopyrimidin-1-yl]propanoate
• CAS: 289712-91-0
• 化学式: C₄₃H₅₃N₄O₁₀P
• 分子量: 816.888
• InChiKey: IYTRYTOKUPSRFV-OEINLCAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  脱氧假尿苷 在 吡啶 、 三乙基碳酸氢铵缓冲液 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.33h， 生成 methyl 5-[2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-β-D-erythro-pentofuranosyl]-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-1-propanoate 3'-(2-cyanoethyl diisopropylphosphoramidite)
  参考文献：
  名称：

  摘要：

  The 2'-deoxypseudouridine (5) was functionalized at N(1) with methyl acrylate by Michael addition. The resulting methyl 2'-deoxypseudouridine-1-propanoate (6) was converted to the phosphoramidite 8 and to the amino-functionalized derivative 9, which was transformed into the fluorescein-labeled phosphoramidites 14 and 16. Fluorescent oligonucleotides were synthesized either from these building blocks or by post-synthetic modification of oligomers containing 2'-deoxypseudouridine subunits. The stability of oligonucleotide duplexes was determined from the melting profiles, measured by UV- or VIS-light absorbance, as well as from the fluorescence emission spectra. While small spacer residues did not affect the thermal stability of the 2'-deoxypseudouridine-containing duplexes, large dye residues led to destabilization.

  DOI：

  10.1002/1522-2675(20000607)83:6<1108::aid-hlca1108>3.0.co;2-9

文献信息

• ——
  作者：Natalya Ramzaeva、Helmut Rosemeyer、Peter Leonard、Klaus Mühlegger、Frank Bergmann、Herbert von der Eltz、Frank Seela

  DOI：10.1002/1522-2675(20000607)83:6<1108::aid-hlca1108>3.0.co;2-9

  日期：2000.6.7

  The 2'-deoxypseudouridine (5) was functionalized at N(1) with methyl acrylate by Michael addition. The resulting methyl 2'-deoxypseudouridine-1-propanoate (6) was converted to the phosphoramidite 8 and to the amino-functionalized derivative 9, which was transformed into the fluorescein-labeled phosphoramidites 14 and 16. Fluorescent oligonucleotides were synthesized either from these building blocks or by post-synthetic modification of oligomers containing 2'-deoxypseudouridine subunits. The stability of oligonucleotide duplexes was determined from the melting profiles, measured by UV- or VIS-light absorbance, as well as from the fluorescence emission spectra. While small spacer residues did not affect the thermal stability of the 2'-deoxypseudouridine-containing duplexes, large dye residues led to destabilization.