1-(2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)thymine | 325145-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)thymine
• 英文别名: 1-[(2S,3R,6S)-3-hydroxy-2-methyl-3,6-dihydro-2H-pyran-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 325145-76-4
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: GCAVDCPFTCRIOJ-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)thymine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以99%的产率得到1-(2',3',6'-trideoxy-β-L-erythro-hexopyranosyl)thymine
  参考文献：
  名称：

  Synthesis and Conformational Studies of Unnatural Pyrimidine Nucleosides

  摘要：

  Starting from 3,4-di-O-acetyl-L-rhamnal (6) and thymine (7) the unsaturated nucleosides 1-(2',3',6'-trideoxy-4'-O-acetyl-alpha- and beta -L-erythro-hex-2'-enopyranosyl)thymine (8a and 8b) were prepared in anomerically pure form. In solution 8a was shown to be present in the H-5(o), and H-0(5) conformations, whereas the predominant conformation of 8b was H-5(o). Chemical transformation of 8a and 8b led to the saturated nucleosides 1-(2',3',6'-trideoxy-alpha- and beta -L-erythro-hexopyranosyl)thymine (10a and 10b, respectively), which were converted into 1-(4'-azido-2',3',4',6'-tetradeoxy-alpha- and beta -L-threohexopyranosyl)thymine (12a and 12b). Preliminary biological studies showed that 9b was inactive against the HIV-1 and HIV-2 viruses.

  DOI：

  10.1080/07328300008544146
• 作为产物：
  描述：

  3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 ammonium sulfate 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 16.5h， 生成 1-(2',3',6'-trideoxy-β-L-erythro-hex-2'-enopyranosyl)thymine
  参考文献：
  名称：

  Synthesis and Conformational Studies of Unnatural Pyrimidine Nucleosides

  摘要：

  Starting from 3,4-di-O-acetyl-L-rhamnal (6) and thymine (7) the unsaturated nucleosides 1-(2',3',6'-trideoxy-4'-O-acetyl-alpha- and beta -L-erythro-hex-2'-enopyranosyl)thymine (8a and 8b) were prepared in anomerically pure form. In solution 8a was shown to be present in the H-5(o), and H-0(5) conformations, whereas the predominant conformation of 8b was H-5(o). Chemical transformation of 8a and 8b led to the saturated nucleosides 1-(2',3',6'-trideoxy-alpha- and beta -L-erythro-hexopyranosyl)thymine (10a and 10b, respectively), which were converted into 1-(4'-azido-2',3',4',6'-tetradeoxy-alpha- and beta -L-threohexopyranosyl)thymine (12a and 12b). Preliminary biological studies showed that 9b was inactive against the HIV-1 and HIV-2 viruses.

  DOI：

  10.1080/07328300008544146

文献信息

• Synthesis and Conformational Studies of Unnatural Pyrimidine Nucleosides
  作者：Ferenc Sztaricskai、Andrea Csorvási、András Horváth、Gyula Batta、Zoltán Dinya

  DOI：10.1080/07328300008544146

  日期：2000.1.1

  Starting from 3,4-di-O-acetyl-L-rhamnal (6) and thymine (7) the unsaturated nucleosides 1-(2',3',6'-trideoxy-4'-O-acetyl-alpha- and beta -L-erythro-hex-2'-enopyranosyl)thymine (8a and 8b) were prepared in anomerically pure form. In solution 8a was shown to be present in the H-5(o), and H-0(5) conformations, whereas the predominant conformation of 8b was H-5(o). Chemical transformation of 8a and 8b led to the saturated nucleosides 1-(2',3',6'-trideoxy-alpha- and beta -L-erythro-hexopyranosyl)thymine (10a and 10b, respectively), which were converted into 1-(4'-azido-2',3',4',6'-tetradeoxy-alpha- and beta -L-threohexopyranosyl)thymine (12a and 12b). Preliminary biological studies showed that 9b was inactive against the HIV-1 and HIV-2 viruses.