(2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate | 622379-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(3,5-dioxo-1,2,4-triazin-2-yl)-4-methyloxolan-2-yl]methyl benzoate
• CAS: 622379-83-3
• 化学式: C₃₀H₂₅N₃O₉
• 分子量: 571.543
• InChiKey: BKPAIHNXFCLIHR-RMAXSRAJSA-N

物化性质

• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate 在 甲醇 、 氨 作用下， 反应 48.0h， 以75%的产率得到2'-C-methyl-6-azauridine
  参考文献：
  名称：

  [EN] NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  [FR] DERIVES NUCLEOSIDIQUES DESTINES AU TRAITEMENT DE L'INFECTION PAR LE VIRUS DE L'HEPATITE C

  摘要：

  公开号：

  WO2003093290A3
• 作为产物：
  描述：

  ALPHA-D-赤式戊呋喃糖-2-酮 1,3,5-三苯甲酸酯 在 4-二甲氨基吡啶 、 四氯化锡 、 牛血清白蛋白 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (2R,3R,4R,5R)-5-((benzoyloxy)methyl)-2-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  2′-C-Alkylribonucleosides: Design, Synthesis, and Conformation

  摘要：

  Certain 2'-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed.

  DOI：

  10.1080/07328319708006205

文献信息

• A Short, Flexible Route toward 2‘-<i>C</i>-Branched Ribonucleosides
  作者：Rogers E. Harry-O'kuru、Jennifer M. Smith、Michael S. Wolfe

  DOI：10.1021/jo961893+

  日期：1997.3.1

  A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-0-benzoyl-alpha-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC drop CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the beta-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.
• [EN] MODIFIED NUCLEOSIDES AND NUCLEOTIDES ANALOGS AS ANTIVIRAL AGENTS FOR CORONA AND OTHER VIRUSES<br/>[FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES MODIFIÉS UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX CONTRE LE CORONAVIRUS ET D'AUTRES VIRUS
  申请人：[en]EMORY UNIVERSITY

  公开号：WO2022217154A2

  公开（公告）日：2022-10-13

  Compounds, compositions and methods for preventing, treating or curing a coronavirus infection in human subjects or other animal hosts. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV-2. In another embodiment, the methods are used to treat a patient infected with a Flavivirus, Picornavus, Togavirus, or Bunyavirus.