3-脱氧-3-甲基-D-呋喃核糖 1,2-二乙酸酯 5-苯甲酸酯 | 444019-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-脱氧-3-甲基-D-呋喃核糖 1,2-二乙酸酯 5-苯甲酸酯
• 中文别名: 3-脱氧-3-甲基-D-呋喃核糖1,2-二乙酸酯5-苯甲酸酯
• 英文名称: 1,2-di-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-D-ribofuranose
• 英文别名: (3R,4R,5S)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3-diyl diacetate；[(2S,3R,4R)-4,5-diacetyloxy-3-methyloxolan-2-yl]methyl benzoate
• CAS: 444019-07-2
• 化学式: C₁₇H₂₀O₇
• 分子量: 336.342
• InChiKey: KWHFDANUMSULSB-HSWPEUCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-脱氧-3-甲基-D-呋喃核糖 1,2-二乙酸酯 5-苯甲酸酯 、 N,N-二苯基-氨基甲酸 2-(乙酰氨基)-9H-嘌呤-6-基酯 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以55%的产率得到2-N-acetyl-9-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)-6-O-diphenylcarbamoylguanine
  参考文献：
  名称：

  Revisited 3′-Deoxy-3′-C-Methyl-β-D-Ribonucleoside Series

  摘要：

  The synthesis of some 3'-deoxy-3'-C-methylnucleoside analogues bearing naturally occuring nucleic acid bases was achieved from the preparation of a suitable peracylated 3-deoxy-3-C-methyl sugar using a stereoselective pathway. In addition, examples of chemical modifications at the 2' position are presented.

  DOI：

  10.1080/15257770701521730
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 3-脱氧-3-甲基-D-呋喃核糖 1,2-二乙酸酯 5-苯甲酸酯
  参考文献：
  名称：

  Revisited 3′-Deoxy-3′-C-Methyl-β-D-Ribonucleoside Series

  摘要：

  The synthesis of some 3'-deoxy-3'-C-methylnucleoside analogues bearing naturally occuring nucleic acid bases was achieved from the preparation of a suitable peracylated 3-deoxy-3-C-methyl sugar using a stereoselective pathway. In addition, examples of chemical modifications at the 2' position are presented.

  DOI：

  10.1080/15257770701521730

文献信息

• Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase
  申请人：——

  公开号：US20020147160A1

  公开（公告）日：2002-10-10

  The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

  本发明提供了核苷化合物及其某些衍生物，这些衍生物是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，可用于治疗RNA依赖性RNA病毒感染。它们特别适用于作为丙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，以及/或用于治疗丙型肝炎感染。本发明还描述了包含这种核苷化合物的药物组合物，单独使用或与其他对RNA依赖性RNA病毒感染，特别是HCV感染有效的制剂组合使用。还公开了使用本发明的核苷化合物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。
• Oligonucleotides having modified nucleoside units
  申请人：——

  公开号：US20040014957A1

  公开（公告）日：2004-01-22

  Disclosed are oligonucleotides and oligonucleosides that include one or more modified nucleoside units. The oligonucleotides and oligonucleosides are particularly useful as antisense agents, ribozymes, aptamer, siRNA agents, probes and primers or, when hybridized to an RNA, as a substrate for RNA cleaving enzymes including RNase H and dsRNase.

  披露的是包括一个或多个修饰核苷单元的寡核苷酸和寡核苷糖。这些寡核苷酸和寡核苷糖特别适用于作为反义剂、核酶、适配体、siRNA试剂、探针和引物，或者当它们与RNA杂交时，作为包括RNase H和dsRNase的RNA切割酶的底物。
• NUCLEOSIDE DERIVATIVES AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYERMASE
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20170183373A1

  公开（公告）日：2017-06-29

  The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

  本发明提供了核苷类化合物及其某些衍生物，这些化合物是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，对于治疗RNA依赖性RNA病毒感染非常有用。它们特别适用于作为乙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，和/或用于治疗丙型肝炎感染。该发明还描述了含有这种核苷类化合物的药物组合物，单独使用或与其他针对RNA依赖性RNA病毒感染，特别是HCV感染的药物一起使用。还公开了使用本发明的核苷类化合物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。
• Synthesis of 3′-deoxy-3′-C-methyl nucleoside derivatives
  作者：Mohamed Aljarah、Sarah Couturier、Christophe Mathé、Christian Périgaud

  DOI：10.1016/j.bmc.2008.06.011

  日期：2008.8

  2',3'-Dideoxy-3'-C-methyl nucleosides bearing the five naturally occurring nucleic acid bases were synthesized. Additionally, the 3'-deoxy-3'-C-methyl nucleoside analogues bearing 5-aminoimidazole-4-carboxamide as well as 1,2,4-triazole-3-carboxamide moieties were prepared. The synthesis of the corresponding 2',3'-dideoxy-3'-C-methyl triazole derivative was also accomplished. The dideoxynucleoside

  合成带有五个天然存在的核酸碱基的2'，3'-二脱氧-3'-C-甲基核苷。另外，制备了带有5-氨基咪唑-4-羧酰胺以及1,2,4-三唑-3-羧酰胺部分的3'-脱氧-3'-C-甲基核苷类似物。还完成了相应的2'，3'-二脱氧-3'-C-甲基三唑衍生物的合成。通过从它们的3'-脱氧-3'-C-甲基母体核糖核苷进行自由基脱氧制备二脱氧核苷衍生物。当在细胞培养实验中评估其抗病毒活性时，这些化合物均未显示任何显着的抗病毒活性。
• Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase
  申请人：——

  公开号：US20040110717A1

  公开（公告）日：2004-06-10

  The present invention provides nucleoside derivatives which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside derivatives alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside derivatives of the present invention.

  本发明提供了一种核苷酸衍生物，其是RNA依赖性RNA病毒聚合酶的抑制剂。这些化合物是RNA依赖性RNA病毒复制的抑制剂，可用于治疗RNA依赖性RNA病毒感染。它们特别适用于作为丙型肝炎病毒（HCV）NS5B聚合酶的抑制剂，作为HCV复制的抑制剂，和/或用于治疗丙型肝炎感染。该发明还描述了含有这种核苷酸衍生物的制药组合物，单独或与其他对RNA依赖性RNA病毒感染活性的制剂结合使用，特别是HCV感染。还揭示了使用本发明的核苷酸衍生物抑制RNA依赖性RNA聚合酶、抑制RNA依赖性RNA病毒复制和/或治疗RNA依赖性RNA病毒感染的方法。