N'-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-hex-1-ynyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N,N-dimethyl-formamidine | 178420-88-7

• 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: N'-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-hex-1-ynyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N,N-dimethyl-formamidine
• CAS: 178420-88-7
• 化学式: C₄₁H₄₅N₅O₅
• 分子量: 687.839
• InChiKey: NPTJVIIGFOYFRF-HKIDPNTFSA-N

物化性质

• 沸点：
  840.5±75.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  51.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  103.46
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 N'-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-hex-1-ynyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N,N-dimethyl-formamidine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以56%的产率得到Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-[4-(dimethylamino-methyleneamino)-5-hex-1-ynyl-pyrrolo[2,3-d]pyrimidin-7-yl]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  7-Deazaadenine-DNA: Bulky 7-Iodo Substituents or Hydrophobic 7-Hexynyl Chains Are Well Accommodated in the Major Groove of Oligonucleotide Duplexes

  摘要：

  Oligonucleotides containing 7-deaza-7-(hex-1-ynyl)-2'-deoxyadenosine (1) and 7-deaza-7-iodo-2'-deoxyadenosine (2) are described. The corresponding phosphoramidites (3 a,b) were synthesized and employed in solid-phase oligonucleotide synthesis. The modified 7-deazaadenine residues show selective base-pairing with dT. According to the T-m values and the thermodynamic data of duplex formation, the 7-iodo and the 7-(hex-1-ynyl) residues of a 7-deazaadenine moiety increase the duplex stability with retention of the particular DNA structure. This is different from 8-substituted adenine, which destabilizes the nucleic acid duplex significantly. The nucleoside 1 fluoresces strongly.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1781::aid-chem1781>3.0.co;2-k
• 作为产物：
  描述：

  7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-(hex-1-ynyl)-1H-pyrrolo[2,3-d]pyrimidin-4-amine 在 嘧啶 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N'-(7-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-5-hex-1-ynyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-N,N-dimethyl-formamidine
  参考文献：
  名称：

  7-Deazaadenine-DNA: Bulky 7-Iodo Substituents or Hydrophobic 7-Hexynyl Chains Are Well Accommodated in the Major Groove of Oligonucleotide Duplexes

  摘要：

  Oligonucleotides containing 7-deaza-7-(hex-1-ynyl)-2'-deoxyadenosine (1) and 7-deaza-7-iodo-2'-deoxyadenosine (2) are described. The corresponding phosphoramidites (3 a,b) were synthesized and employed in solid-phase oligonucleotide synthesis. The modified 7-deazaadenine residues show selective base-pairing with dT. According to the T-m values and the thermodynamic data of duplex formation, the 7-iodo and the 7-(hex-1-ynyl) residues of a 7-deazaadenine moiety increase the duplex stability with retention of the particular DNA structure. This is different from 8-substituted adenine, which destabilizes the nucleic acid duplex significantly. The nucleoside 1 fluoresces strongly.

  DOI：

  10.1002/(sici)1521-3765(19980904)4:9<1781::aid-chem1781>3.0.co;2-k