3'-O-(4,4'-dimethoxytrityl)-5'-O-{[2-(4-nitrophenyl)ethoxy]carbonyl}thymidine | 199792-94-4

• 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: 3'-O-(4,4'-dimethoxytrityl)-5'-O-{[2-(4-nitrophenyl)ethoxy]carbonyl}thymidine
• 英文别名: [(2R,3S,5R)-3-[bis(4-methoxyphenyl)-phenylmethoxy]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 2-(4-nitrophenyl)ethyl carbonate
• CAS: 199792-94-4
• 化学式: C₄₀H₃₉N₃O₁₁
• 分子量: 737.763
• InChiKey: RIYIQZHPZSHSIF-LIVOIKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3'-O-(4,4'-dimethoxytrityl)-5'-O-{[2-(4-nitrophenyl)ethoxy]carbonyl}thymidine 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到3’-O-(4,4’-二甲氧基三苯甲基)胸苷
  参考文献：
  名称：

  An Inverse Approach in Oligodeoxyribonucleotide Synthesis

  摘要：

  We synthesized 3'-O-dimethoxytrityl-5'O-phosphoramidites and 5'-O-succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.

  DOI：

  10.1080/07328319708006249
• 作为产物：
  描述：

  2-(4-nitrophenyl)ethoxycarbonyl chloride 在 吡啶 作用下， 反应 4.0h， 生成 3'-O-(4,4'-dimethoxytrityl)-5'-O-{[2-(4-nitrophenyl)ethoxy]carbonyl}thymidine
  参考文献：
  名称：

  An Inverse Approach in Oligodeoxyribonucleotide Synthesis

  摘要：

  We synthesized 3'-O-dimethoxytrityl-5'O-phosphoramidites and 5'-O-succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.

  DOI：

  10.1080/07328319708006249

文献信息

• An Inverse Approach in Oligodeoxyribonucleotide Synthesis
  作者：Thomas Wagner、Wolfgang Pfleiderer

  DOI：10.1080/07328319708006249

  日期：1997.7

  We synthesized 3'-O-dimethoxytrityl-5'O-phosphoramidites and 5'-O-succinates which can be used as monomeric building blocks for the built up of oligodeoxyribonucleotides in the alternative 5'-3' direction. With this inverse strategy oligonucleotide 3'-conjugates as well as 3'-3' and 5'-5' internucleotidic linkages can be easily formed.
• Nucleotides, Part LXV, Synthesis of 2′-Deoxyribonucleoside 5′-Phosphoramidites: New Building Blocks for the Inverse (5′-3′)-Oligonucleotide Approach
  作者：Thomas Wagner、Wolfgang Pfleiderer

  DOI：10.1002/1522-2675(20000809)83:8<2023::aid-hlca2023>3.0.co;2-p

  日期：2000.8.9

  The syntheses of the 3'-O-(4,4'-dimethoxytrityl)-protected 5'-phosphoramidites 25-28 and 5'-(hydrogen succinates) 29-32, which can be used as monomeric building blocks for the inverse (5'-3')-oligodeoxyribonucleotide synthesis are described (Scheme). These activated nucleosides and nucleotides were obtained by two slightly different four-step syntheses starting with the base-protected nucleosides 13-20. For the protection of the aglycon residues, the well-established 2-(4-nitrophenyl)ethyl (npe) and [2-(4-nitrophenyl)ethoxy]carbonyl (npeoc) groups were used. The assembly of the oligonucleotides required a slightly increased coupling time of 3 min in application of the common protocol (see Table 1). The use of pyridinium hydrochloride as an activator (instead of 1H-tetrazole) resulted in an extremely shorter activation time of 30 seconds. We established the efficiency of this inverse strategy by the synthesis of the oligonucleotide 3'-conjugates 33 and 34 which carry lipophilic caps derived from cholesterol and vitamin E, respectively, as well as by the formation of (3'-3')- and (5'-5')-internucleotide linkages (see Table 2).