N2',O3'-carbonyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-(methylamino)uridine | 852333-54-1

• 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: N2',O3'-carbonyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-(methylamino)uridine
• 英文别名: 1-[(3aR,4R,6R,6aS)-6-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-methyl-2-oxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]oxazol-4-yl]pyrimidine-2,4-dione
• CAS: 852333-54-1
• 化学式: C₃₂H₃₁N₃O₈
• 分子量: 585.613
• InChiKey: WIGXHSYFUZDBQR-YXINZVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,2'-anhydro-3'-O-(N-methylcarbamoyl)-5'-O-(4,4'-dimethoxytrityl)uridine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到N2',O3'-carbonyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-(methylamino)uridine
  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