1-((2R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-cyclopropyl-1H-pyrimidine-2,4-dione | 175470-87-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 1-((2R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-cyclopropyl-1H-pyrimidine-2,4-dione
• 英文别名: 5-cyclopropyl-1-[(2R,4S,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• CAS: 175470-87-8
• 化学式: C₂₆H₂₈N₂O₄S
• 分子量: 464.585
• InChiKey: KZKCZLVGWUIMNC-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-cyclopropyl-1H-pyrimidine-2,4-dione 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5-cyclopropyl-2'-deoxy-4'-thio-β-uridine
  参考文献：
  名称：

  Synthesis and Anti-Herpes Virus Activity of 2‘-Deoxy-4‘-thiopyrimidine Nucleosides

  摘要：

  A series of 5-substituted 2'-deoxy-4'-thiopyrimidine nucleosides was synthesized and evaluated as potential antiviral agents. A number of analogues such as 2'-deoxy-5-propyl-4'-thiouridine (3ii), 2'-deoxy-5-isopropyl-4'-thiouridine (3iii), 5-cyclopropyl-2'-deoxy-4'-thiouridine (3iv), 2'-deoxy-4'-thio-5-vinyluridine (3viii), and 5-(2-chloroethyl)-2'-deoxy-4'-thiouridin (3xx) were found to be highly active against herpes simplex virus type-1 (HSV-1) and varicella tester virus (VZV) in vitro with no significant cytotoxicity. The compound with the broadest spectrum of activity was 2'-deoxy-5-ethyl-4'-thiouridine (3i) which showed significant activity against HSV-1, HSV-2, and VZV.

  DOI：

  10.1021/jm950029r
• 作为产物：
  描述：

  5-cyclopropyluracil 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 生成 1-((2R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-5-cyclopropyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  The Synthesis of Some 5-Alkyl (Cycloalkyl)-Substituted 2′ -Deoxy-4′-Thiouridines

  摘要：

  The silylated pyrimidine bases IIa-d were condensed with the benzyl 3,5-di-O-benzyl-2-deoxy-1,4-ditkio-D-erythro-pentofuranoside III in acetonitrile under activation by N-iodosuccinimide, giving ca 1.5 : 1/alpha: beta anomeric mixtures of the blocked nucleosides IVa-d and Va-d. in yields of 55-88%. After the separation on a silica column the pure anomers were deprotected by BCl3 or TiCl4, providing the free nucleosides VIa-d and VIIa,c,d in moderate to good overall yields. The beta- or alpha-anomeric configuration, anti-glycosidic conformation and prevailing C2'-endo(S) thiosugar pucker in the synthesized compounds were established by the combined use of the H-1, C-13 NMR and X-ray crystallography.

  DOI：

  10.1080/07328319608002375