1-((2S,4R,5S,6R)-4-Benzotriazol-1-yl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-((2S,4R,5S,6R)-4-Benzotriazol-1-yl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
• 英文别名: 1-[(2S,4R,5S,6R)-4-(benzotriazol-1-yl)-5-hydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]-5-methyl-pyrimidine-2,4-dione；1-[(2S,4R,5S,6R)-4-(benzotriazol-1-yl)-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₇H₁₉N₅O₅
• 分子量: 373.368
• InChiKey: ORUAWBVOGKUPNV-KBXIAJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  在 氨 作用下， 以69%的产率得到1-((2S,4R,5S,6R)-4-Benzotriazol-1-yl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of 3'-Azolyl-2',3'-dideoxyhexose Nucleosides.

  摘要：

  1,8-Diazabicyclo[5.4.0]undec-7-ene salts of 2-methyl-4(5)-nitroimidazole or benzotriazole were obtained in crystalline form. Michael-type addition of these salts to (4S,5R)-(E)-4,6-di-O-acetyl-5-hydroxy-2-hexenal gave, after acetylation of the product, an isomeric mixture of acetylated 3-(azol-1-yl)-2,3-dideoxy-D-arabino-hexopyranosides and 3-(azol-1-yl)-2,3-dideoxy-D-ribo-hexofuranosides. Reaction of these peracetylated adducts with trimethylsilylated thymine in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflale) afforded the corresponding nucleosides which were deprotected by using methanolic ammonia. The nucleosides were found inactive against HIV-I and HSV-1.

  DOI：

  10.3891/acta.chem.scand.52-0935

文献信息

• Synthesis of 3'-Azolyl-2',3'-dideoxyhexose Nucleosides.
  作者：Krzysztof Walczak、Erik B. Pedersen、Claus Nielsen、Thomas Schultz、Kristian O. Sylvester-Hvid、Kenneth J. Klabunde、Kurt V. Mikkelsen、Alexander Senning

  DOI：10.3891/acta.chem.scand.52-0935

  日期：——

  1,8-Diazabicyclo[5.4.0]undec-7-ene salts of 2-methyl-4(5)-nitroimidazole or benzotriazole were obtained in crystalline form. Michael-type addition of these salts to (4S,5R)-(E)-4,6-di-O-acetyl-5-hydroxy-2-hexenal gave, after acetylation of the product, an isomeric mixture of acetylated 3-(azol-1-yl)-2,3-dideoxy-D-arabino-hexopyranosides and 3-(azol-1-yl)-2,3-dideoxy-D-ribo-hexofuranosides. Reaction of these peracetylated adducts with trimethylsilylated thymine in the presence of trimethylsilyl trifluoromethanesulfonate (TMS triflale) afforded the corresponding nucleosides which were deprotected by using methanolic ammonia. The nucleosides were found inactive against HIV-I and HSV-1.