1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)uracil | 959843-61-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)uracil
• 英文别名: ((2S,3R,4R,5R)-4-Acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-methyltetrahydrofuran-2-yl)methyl benzoate；[(2S,3R,4R,5R)-4-acetyloxy-5-(2,4-dioxopyrimidin-1-yl)-3-methyloxolan-2-yl]methyl benzoate
• CAS: 959843-61-9
• 化学式: C₁₉H₂₀N₂O₇
• 分子量: 388.377
• InChiKey: KWMCSOIGFGMSOD-MDNXKNQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)uracil 在 吡啶 、 溶剂黄146 、 肼 、 4-二甲氨基吡啶 、 硫代氯甲酸苯酯 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1-(5-O-benzoyl-2,3-dideoxy-3-C-methyl-β-D-erythro-pentofuranosyl)uracil
  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：

  3-脱氧-3-甲基-D-呋喃核糖 1,2-二乙酸酯 5-苯甲酸酯 、 尿嘧啶 在 硫酸氢铵 、 六甲基二硅氮烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以85%的产率得到1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)uracil
  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

• 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。
• Synthesis of 3′-deoxy-3′-C-methyl-β-d-ribonucleoside analogs
  作者：Sarah Couturier、Mohamed Aljarah、Gilles Gosselin、Christophe Mathé、Christian Périgaud

  DOI：10.1016/j.tet.2007.08.092

  日期：2007.11

  3'-Deoxy-3'-C-methyl-beta-D-ribonucleoside analogs bearing the five canonical bases of nucleic acids have been synthesized. All these derivatives were prepared by glycosylation of the corresponding heterocyclic bases with a suitable peracylated 3-C-methyl sugar precursor. The synthesis of the 3-C-methyl sugar precursor is described following a new stereoselective synthetic pathway. (C) 2007 Elsevier Ltd. All rights reserved.