2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-4-O-(4-nitrophenyl)uridine | 215460-54-1

• 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: 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-4-O-(4-nitrophenyl)uridine
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-4-(4-nitrophenoxy)pyrimidin-2-one
• CAS: 215460-54-1
• 化学式: C₃₆H₃₃N₃O₉
• 分子量: 651.673
• InChiKey: FURCKXVNBKLTQO-VOTWKOMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.62
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  144.41
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-4-O-(4-nitrophenyl)uridine 在 吡啶 、 二氯乙酸 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2'-deoxy-3'-O-levulinoyl-4-O-(4-nitrophenyl)uridine
  参考文献：
  名称：

  Individual Isomers of Dinucleoside Boranophosphates as Synthons for Incorporation into Oligonucleotides: Synthesis and Configurational Assignment

  摘要：

  Individual isomers of the protected boranophosphates 5a and 5b, i.e, the N-6-benzyl-2'-deoxy-5'- O-(4,4'-dimethoxytrityl)adenosin-3'-yl 2'-deoxy-4-O-(4-nitrophenyl)uridin-5'-yl boranophosphates, were synthesized via stereospecific silylation and boronation of their H-phosphonate precursors. 2D-NMR Spectroscopic studies yielded an initial assignment of the isomer configuration, which was further confirmed unambiguously by a parallel chemical synthesis. Deprotection of the 'dimers' 5a and 5b yielded the individual [P(R)]- and [P(S)]-isomers 7a and 7b, respectively, i.e., the 2'-deoxyadenosin-3'-yl 2'-deoxycytidin-5'-yl boranophosphates. Their substrate properties toward phosphodiesterase I were identical to those of the previously characterized isomers of dithymidine boranophosphate. The protected 'dimers' 5a and Sb can be used as synthons to incorporate the boranophosphate linkage with a defined configuration to selected positions of an oligonucleotide chain.

  DOI：

  10.1002/1522-2675(20000705)83:7<1377::aid-hlca1377>3.0.co;2-s
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 4-(p-nitrophenoxy)-1-(β-D-2-deoxyribofuranosyl)pyrimidin-2(1H)-one 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 2.0h， 以78%的产率得到2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-4-O-(4-nitrophenyl)uridine
  参考文献：
  名称：

  Individual Isomers of Dinucleoside Boranophosphates as Synthons for Incorporation into Oligonucleotides: Synthesis and Configurational Assignment

  摘要：

  Individual isomers of the protected boranophosphates 5a and 5b, i.e, the N-6-benzyl-2'-deoxy-5'- O-(4,4'-dimethoxytrityl)adenosin-3'-yl 2'-deoxy-4-O-(4-nitrophenyl)uridin-5'-yl boranophosphates, were synthesized via stereospecific silylation and boronation of their H-phosphonate precursors. 2D-NMR Spectroscopic studies yielded an initial assignment of the isomer configuration, which was further confirmed unambiguously by a parallel chemical synthesis. Deprotection of the 'dimers' 5a and 5b yielded the individual [P(R)]- and [P(S)]-isomers 7a and 7b, respectively, i.e., the 2'-deoxyadenosin-3'-yl 2'-deoxycytidin-5'-yl boranophosphates. Their substrate properties toward phosphodiesterase I were identical to those of the previously characterized isomers of dithymidine boranophosphate. The protected 'dimers' 5a and Sb can be used as synthons to incorporate the boranophosphate linkage with a defined configuration to selected positions of an oligonucleotide chain.

  DOI：

  10.1002/1522-2675(20000705)83:7<1377::aid-hlca1377>3.0.co;2-s