1-<5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-β-D-erythro-pemtofuranosyl>5-trifluoromethyluracil | 160452-61-9

• 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-<5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-β-D-erythro-pemtofuranosyl>5-trifluoromethyluracil
• CAS: 160452-61-9
• 化学式: C₁₈H₂₇F₃N₂O₅SSi
• 分子量: 468.569
• InChiKey: NMODPSWOLOBLTI-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  90.39
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-<5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-β-D-erythro-pemtofuranosyl>5-trifluoromethyluracil 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以88%的产率得到1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)-5-trifluoromethyluracil
  参考文献：
  名称：

  Syntheses and Antitumor Activities of D-and L-2′-Deoxy-4′-thio Pyrimidine Nucleosides

  摘要：

  Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio-beta-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L-enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-alpha,beta-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.

  DOI：

  10.1080/15257779408012157
• 作为产物：
  描述：

  5-O-acetyl-3-O-tert-butyldimethylsilyl-2-deoxy-4-thio-D-erythro-pentofuranoside 、 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine 在 四氯化锡 作用下， 以 乙腈 为溶剂， 以81%的产率得到1-<5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-α-D-erythro-pemtofuranosyl>5-trifluoromethyluracil
  参考文献：
  名称：

  Syntheses and Antitumor Activities of D-and L-2′-Deoxy-4′-thio Pyrimidine Nucleosides

  摘要：

  Both enantiomers of 2'-deoxy-4'-thiouridine (9) and 15, 4'-thiothymidine (10) and 16, and 2'-deoxy-4'-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio-beta-D-erythro-pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D- or L-enantiomers of ethyl 5-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4-thio-alpha,beta-xylofuranoside (1) or 18 and 2,4-bis(trimethylsilyloxy)pyrimidine in the presence of SnCl4 in acetonitrile. Cytotoxicities against L-1210 and KB-cells for the compounds 9, 10, 11, 14, 15, 16, and 17 were examined. The compounds 10 and 11 were potentially active.

  DOI：

  10.1080/15257779408012157