1-(2',3',6'-trideoxy-α-L-erythro-hexopyranosyl)thymine | 325145-72-0

• 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-α-L-erythro-hexopyranosyl)thymine
• 英文别名: 1-[(2R,5R,6S)-5-hydroxy-6-methyloxan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 325145-72-0
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: GRCGQODLEPKSJK-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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-α-L-erythro-hexopyranosyl)thymine 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1-(4'-azido-2',3',6'-trideoxy-α-L-threo-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：

  1-(4'-O-acetyl-2',3',6'-trideoxy-β-L-erythro-hex-2-enopyranosyl)thymidine 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 1-(2',3',6'-trideoxy-α-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