5'-O-(4,4'-dimethoxytrityl)-3'-C-aminomethylthymidine | 179178-35-9

• 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: 5'-O-(4,4'-dimethoxytrityl)-3'-C-aminomethylthymidine
• 英文别名: 1-[(2R,4R,5R)-4-(aminomethyl)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 179178-35-9
• 化学式: C₃₂H₃₅N₃O₇
• 分子量: 573.646
• InChiKey: JXQBRWHBAJVSGU-QIBDARBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-C-aminomethylthymidine 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-C-trifluoroacetamidomethylthymidine 3'-(2-cyanoethyl-N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-C-Aminomethyl-and 3′-C-Amethylthymidine

  摘要：

  3'-C-Aminomethyl- and 3'-C-methylthymidine were synthesized and incorporated into oligodeoxynucleotides. Hybridization and enzyme stability of the modified oligonucleotides containing the 3'-C-branched thymidines are discussed.

  DOI：

  10.1080/07328319708001361
• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine 在 4-二甲氨基吡啶 、 氨 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 paraffin 为溶剂， 反应 26.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-3'-C-aminomethylthymidine
  参考文献：
  名称：

  Synthesis and Evaluation of Oligodeoxynucleotides Containing 3′-C-Aminomethyl-and 3′-C-Amethylthymidine

  摘要：

  3'-C-Aminomethyl- and 3'-C-methylthymidine were synthesized and incorporated into oligodeoxynucleotides. Hybridization and enzyme stability of the modified oligonucleotides containing the 3'-C-branched thymidines are discussed.

  DOI：

  10.1080/07328319708001361

文献信息

• Sugar modified nucleosides and their use for synthesis of
  申请人：ICN Pharmaceuticals

  公开号：US05712378A1

  公开（公告）日：1998-01-27

  A number of modified nucleosides are disclosed composed of modified sugar moieties which contain substituents at C1 and C4 positions, or branched substituents at C3 and C5 positions of deoxyribose or ribose. Each nucleoside is converted to or properly protected and then converted to the corresponding phosphoramidites. These phosphoramidites are used to assemble oligonucleotides in which there is at least one of the forenoted nucleosides. These sugar modified oligonucleotides have the potential to be used as antisense therapies since they are expected to enhance nuclease resistance and cellular uptake while they maintain sequence-specificity and affinity to nucleic acid targets in vitro or in vivo.

  本发明揭示了一些改性核苷酸，由改性糖基组成，其中包含在脱氧核糖或核糖的C1和C4位置具有取代基，或在C3和C5位置具有分支取代基。每个核苷酸都被转化或适当保护，然后转化为相应的磷酰胺酯。这些磷酰胺酯用于组装寡核苷酸，在其中至少有一个上述核苷酸。这些糖修饰的寡核苷酸具有作为反义疗法的潜力，因为它们预计能够增强核酸酶抵抗力和细胞摄取，同时在体内或体外维持序列特异性和亲和力与核酸靶标。
• Sugar modified nucleosides
  申请人：Valeant Pharmaceuticals International

  公开号：US06743902B1

  公开（公告）日：2004-06-01

  A number of modified nucleosides are disclosed composed of modified sugar moieties which contain substituents at C1 and C4 positions, or branched substituents at C3 and C5 positions of deoxyribose or ribose. Each nucleoside is converted to or properly protected and then converted to the corresponding phosphoramidites. These phosphoramidites are used to assemble oligonucleotides in which there is at least one of the forenoted nucleosides. These sugar modified oligonucleotides have the potential to be used as antisense therapies since they are expected to enhance nuclease resistance and cellular uptake while they maintain sequence-specificity and affinity to nucleic acid targets in vitro or in vivo.

  本文披露了一些修饰过的核苷酸，由修饰过的糖基组成，其中包含在脱氧核糖或核糖的C1和C4位置，或在C3和C5位置有支链取代基。每个核苷酸都被转化或适当保护，然后转化为相应的磷酰胺酯。这些磷酰胺酯用于组装寡核苷酸，在其中至少有一个上述核苷酸。这些糖修饰的寡核苷酸具有成为反义疗法的潜力，因为预计它们将增强核酸酶的抵抗力和细胞摄取能力，同时在体外或体内保持序列特异性和亲和力与核酸靶标。
• US5712378A
  申请人：——

  公开号：US5712378A

  公开（公告）日：1998-01-27
• US6191266B1
  申请人：——

  公开号：US6191266B1

  公开（公告）日：2001-02-20
• US6743902B1
  申请人：——

  公开号：US6743902B1

  公开（公告）日：2004-06-01