[(2R,3R,4R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)tetrahydrofuran-2-yl]methyl 2-methylpropanoate | 852612-28-3

• 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: [(2R,3R,4R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)tetrahydrofuran-2-yl]methyl 2-methylpropanoate
• 英文别名: isobutyryl(-2)[isobutyryl(-3)][isobutyryl(-5)]Ribf(b)-uracil-1-yl；[(2R,3R,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)oxolan-2-yl]methyl 2-methylpropanoate
• CAS: 852612-28-3
• 化学式: C₂₁H₃₀N₂O₉
• 分子量: 454.477
• InChiKey: GOEVESWXRGOKTQ-MWQQHZPXSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)tetrahydrofuran-2-yl]methyl 2-methylpropanoate 在 copper(l) iodide 、 四(三苯基膦)钯 、 ammonium cerium (IV) nitrate 、 碘 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  5-(Perylen-3-ylethynyl)uracil Derivatives Inhibit Reproduction of Respiratory Viruses

  摘要：

  In this work, we describe the synthesis of 5-(perylen-3-ylethynyl)uridine and its ability to effectively inhibit the replication of respiratory disease pathogens in cell culture, namely: influenza A virus (IVA); type 3 parainfluenza virus (PIV-3); and human respiratory syncytial virus (RSV). Related known compounds were also analyzed: 5-(perylen-3-ylethynyl)-2 '-deoxy-uridine; 5-(perylen-3-ylethynyl)-arabino-uridine; and 1-carboxymethyl-3-pivaloyloxymethyl-5-(perylen-3-ylethynyl)uracil.

  DOI：

  10.1134/s1068162020030139
• 作为产物：
  描述：

  胞苷 在 吡啶 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 反应 14.0h， 生成 [(2R,3R,4R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-bis(2-methylpropanoyloxy)tetrahydrofuran-2-yl]methyl 2-methylpropanoate
  参考文献：
  名称：

  Hydrothermal Deamidation of 4-N-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters

  摘要：

  [GRAPHICS]N,O-Peracylated cytidine and 2'-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 degrees C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

  DOI：

  10.1021/ol0518378

文献信息

• [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO<br/>[FR] N4-HYDROXYCYTIDINE ET DÉRIVÉS ET LEURS UTILISATIONS ANTI-VIRALES
  申请人：UNIV EMORY

  公开号：WO2019113462A1

  公开（公告）日：2019-06-13

  This disclosure relates to certain N4-hydroxycytidine derivatives, pharmaceutical compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections, such as Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infection with the disclosed compounds.

  本公开涉及某些N4-羟基胞苷衍生物、药物组合物以及相关方法。在某些实施例中，本公开涉及使用所述化合物治疗或预防病毒感染，如东部、西部和委内瑞拉马脑炎（EEE、WEE和VEE）、基孔肯雅热（CHIK）、埃博拉、流感、RSV和寨卡病毒感染。
• [EN] N4-HYDROXYCYTIDINE AND DERIVATIVES AND ANTI-VIRAL USES RELATED THERETO<br/>[FR] N4-HYDROXYCYTIDINE ET SES DÉRIVÉS ET UTILISATIONS ANTIVIRALES ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2021159044A1

  公开（公告）日：2021-08-12

  This disclosure relates to certain N4-hydroxycytidine derivatives, pharmaceutical compositions, and methods related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of human coronavirus 2019-nCoV.

  这项披露涉及某些N4-羟基胞苷衍生物、药物组合物以及相关方法。在某些实施方式中，该披露涉及治疗或预防人类冠状病毒2019-nCoV。
• [EN] 4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES À BASE DE NUCLÉOSIDES ET DE NUCLÉOTIDES CONTENANT DU 4-HALOGÈNE ET UTILISATIONS ASSOCIÉES
  申请人：UNIV EMORY

  公开号：WO2021137913A3

  公开（公告）日：2021-09-30
• WO2019173602A5
  申请人：——

  公开号：WO2019173602A5

  公开（公告）日：2022-03-14
• Selective Removal of the 2‘- and 3‘-<i>O</i>-Acyl Groups from 2‘,3‘,5‘-Tri-<i>O</i>-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹
  作者：Ireneusz Nowak、Carl T. Jones、Morris J. Robins

  DOI：10.1021/jo0600104

  日期：2006.4.1

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.