5-Chloro-1-((2R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1H-pyrimidine-2,4-dione | 459448-63-6

• 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: 5-Chloro-1-((2R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1H-pyrimidine-2,4-dione
• 英文别名: 5-chloro-1-[(2R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]pyrimidine-2,4-dione
• CAS: 459448-63-6
• 化学式: C₁₀H₁₃ClN₂O₆
• 分子量: 292.676
• InChiKey: LBOIOEIFWYTWRG-XUTVFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-Chloro-1-((2R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-1H-pyrimidine-2,4-dione 在 4-二甲氨基吡啶 、 tetrafluoroboric acid 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Toluene-4-sulfonic acid (4aR,6R,8R,8aR)-6-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  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 三氟甲磺酸三甲基硅酯 、 氨 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.0h， 生成 5-Chloro-1-((2R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-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

文献信息

• SYNTHESIS OF 3′-AZIDO-2′,3′- DIDEOXY-4′-KETOHEXOPYRANOID ANALOGUES AS POSSIBLE ANTIVIRAL NUCLEOSIDES
  作者：Abdul R. Khan、Kimberly X. Mulligan、Kinfe K. Redda、Abraham P. Ollapally

  DOI：10.1081/scc-120003150

  日期：2002.1

  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.