N-(9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-[(R)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-acetamide | 253586-26-4

• 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: N-(9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-[(R)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-acetamide
• CAS: 253586-26-4
• 化学式: C₄₂H₄₂N₆O₁₁
• 分子量: 806.829
• InChiKey: AVNFYJGLPFRMTC-SQCUQKGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  59.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  211.42
• 氢给体数：
  3.0
• 氢受体数：
  14.0

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-(9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-[(R)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-acetamide 生成 Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(R)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Fast and Reliable Automated Synthesis of RNA and Partially 2′-O- Protected Precursors (`Caged RNA') Based on Two Novel, Orthogonal 2′-O-Protecting Groups, Preliminary Communication

  摘要：

  Two sets of RNA phosphoramidites. carrying the (fluoride-labile) 2'-O-[(triisopropylsilyl)oxy]methyl (=tom) group and the (photolabile) [(R)-1-(2-nitrophenyl)ethoxy]methyl (=(R)-npeom) group, were prepared (see 1-4 and 5-8, resp.). The two protecting groups were completely orthogonal to each other. Three ribozyme-substrate constructs, protected each by a (R)-npeom group, were synthesized; on photolysis, efficient cleavage of this remaining protecting group occurred (Scheme 3). It could be demonstrated that the presence of one (R)-npeom group within a RNA strand has only a minor influence on the pairing properties of corresponding duplexes.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1753::aid-hlca1753>3.0.co;2-y
• 作为产物：
  描述：

  (-)-1-(2-硝基苯基)乙醇 在 磺酰氯 、 二丁基二氯化锡 、 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 146.5h， 生成 N-(9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-[(R)-1-(2-nitro-phenyl)-ethoxymethoxy]-tetrahydro-furan-2-yl}-6-oxo-6,9-dihydro-1H-purin-2-yl)-acetamide
  参考文献：
  名称：

  Fast and Reliable Automated Synthesis of RNA and Partially 2′-O- Protected Precursors (`Caged RNA') Based on Two Novel, Orthogonal 2′-O-Protecting Groups, Preliminary Communication

  摘要：

  Two sets of RNA phosphoramidites. carrying the (fluoride-labile) 2'-O-[(triisopropylsilyl)oxy]methyl (=tom) group and the (photolabile) [(R)-1-(2-nitrophenyl)ethoxy]methyl (=(R)-npeom) group, were prepared (see 1-4 and 5-8, resp.). The two protecting groups were completely orthogonal to each other. Three ribozyme-substrate constructs, protected each by a (R)-npeom group, were synthesized; on photolysis, efficient cleavage of this remaining protecting group occurred (Scheme 3). It could be demonstrated that the presence of one (R)-npeom group within a RNA strand has only a minor influence on the pairing properties of corresponding duplexes.

  DOI：

  10.1002/(sici)1522-2675(19991006)82:10<1753::aid-hlca1753>3.0.co;2-y