2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine | 199793-01-6

• 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-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine
• 英文别名: 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine
• CAS: 199793-01-6
• 化学式: C₄₈H₄₅N₇O₁₂
• 分子量: 911.925
• InChiKey: AMAPXAOONJYCAD-FEWNNGCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  67.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  234.59
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine 在 四氮唑 作用下， 以 乙腈 为溶剂， 以83%的产率得到2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N²-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine 5'-(2-cyanoethyl diisopropylphosphoramidite)
  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：

  Carbonic acid (2R,3S,5R)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 2-(5-dimethylamino-naphthalene-1-sulfonyl)-ethyl ester 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 0.02h， 以95%的产率得到2'-deoxy-3'-O-(4,4'-dimethoxytrityl)-N2-{[2-(4-nitrophenyl)ethoxy]carbonyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine
  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

• 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).