2'-(anthraquinon-2-ylcarboxamido)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-N-methyluridine | 852333-56-3

• 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: 2'-(anthraquinon-2-ylcarboxamido)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-N-methyluridine
• 英文别名: N-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]-N-methyl-9,10-dioxoanthracene-2-carboxamide
• CAS: 852333-56-3
• 化学式: C₄₆H₃₉N₃O₁₀
• 分子量: 793.83
• InChiKey: XGZXXMUZXHUCPX-FWUQRYMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  59
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2'-(anthraquinon-2-ylcarboxamido)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-N-methyluridine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 4 A molecular sieve 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以58%的产率得到2'-(anthraquinon-2-ylcarboxamido)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-N-methyluridin-3-'yl-(2-cyanoethyl)-N,N-diisopropylphosphoramidite
  参考文献：
  名称：

  3‘-Immobilized Probes with 2‘-Caps:  Synthesis of Oligonucleotides with 2‘-N-Methyl-2‘-(anthraquinone carboxamido)uridine Residues

  摘要：

  A synthesis for oligodeoxynucleotides with a 3'-terminal 2'-N-methyl-2'-acylamido-2'-deoxyuridine residue was developed. Unlike their unmethylated counterparts, these oligodeoxynucleotides can be stably immobilized on aldehyde-displaying glass surfaces to provide DNA microarrays. An anthraquinone carboxamido group as a 2'-substituent doubled the capture efficiency of an immobilized tetradecamer.

  DOI：

  10.1021/ol0502432
• 作为产物：
  描述：

  N2',O3'-carbonyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-(methylamino)uridine 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 2'-(anthraquinon-2-ylcarboxamido)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-N-methyluridine
  参考文献：
  名称：

  3‘-Immobilized Probes with 2‘-Caps:  Synthesis of Oligonucleotides with 2‘-N-Methyl-2‘-(anthraquinone carboxamido)uridine Residues

  摘要：

  A synthesis for oligodeoxynucleotides with a 3'-terminal 2'-N-methyl-2'-acylamido-2'-deoxyuridine residue was developed. Unlike their unmethylated counterparts, these oligodeoxynucleotides can be stably immobilized on aldehyde-displaying glass surfaces to provide DNA microarrays. An anthraquinone carboxamido group as a 2'-substituent doubled the capture efficiency of an immobilized tetradecamer.

  DOI：

  10.1021/ol0502432