1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil | 138560-08-4

• 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-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil
• CAS: 138560-08-4
• 化学式: C₁₁H₁₄N₂O₅S
• 分子量: 286.309
• InChiKey: YAOYZGGAQYQQLZ-QXFUBDJGSA-N

物化性质

• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.54
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  101.39
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil 在 4-二甲氨基吡啶 、 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 0.17h， 生成 4-(1,2,4-triazol-1-yl)-1-(3,5-di-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)pyrimidin-2(1H)-one
  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 在 四丁基氟化铵 、 四氯化锡 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 1-(5-O-acetyl-2-deoxy-4-thio-β-D-erythro-pentofuranosyl)uracil
  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

文献信息

• Stereocontrolled preparation of cyclic xanthate; a novel synthetic route to 4-thiofuranose and 4′-thionucleoside
  作者：Jun'ichi Uenishi、Mitsuhiro Motoyama、Yoshitaka Nishiyama、Shoji Wakabayashi

  DOI：10.1039/c39910001421

  日期：——

  Optically active cyclic xanthate was prepared by the reaction of an epoxy alcohol with NaH and CS2, and was found to be a useful intermediate for synthesis of 4-thio-2-deoxyribose and 4′-thio-2′-deoxyribonucleoside.

  通过环氧醇与 NaH 和 CS2 的反应制备了具有光学活性的环黄原酸盐，并发现它是合成 4-硫代-2-脱氧核糖和 4â²-硫代-2â²-脱氧核苷的有用中间体。
• NUCLEOSIDES & NUCLEOTIDES, 1994, 13, 1347-1361
  作者：

  DOI：——

  日期：——