1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione | 459448-74-9

• 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-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione
• CAS: 459448-74-9
• 化学式: C₁₀H₁₂FN₅O₅
• 分子量: 301.234
• InChiKey: VVYKFBSGOYQLEV-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.0
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  153.31
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 3 A molecular sieve 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 5-fluoro-1-(3-azido-2,3-dideoxy-6-O-trityl-β-D-erythro-hexopyranos-4-ulosyl)uracil
  参考文献：
  名称：

  SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES

  摘要：

  Peracetylated 2-deoxy-D-glucose was coupled with silylated bases. The product was deacetylated and the 4',6'-hydroxy groups were then protected. An azido group was introduced at the 3-carbon via tosylation, followed by deprotection, tritylation, and oxidation to give the final compound.

  DOI：

  10.1081/scc-120003150
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose 在 4-二甲氨基吡啶 、 tetrafluoroboric acid 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 氨 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 43.0h， 生成 1-((2R,4S,5S,6R)-4-Azido-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-5-fluoro-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES

  摘要：

  Peracetylated 2-deoxy-D-glucose was coupled with silylated bases. The product was deacetylated and the 4',6'-hydroxy groups were then protected. An azido group was introduced at the 3-carbon via tosylation, followed by deprotection, tritylation, and oxidation to give the final compound.

  DOI：

  10.1081/scc-120003150