5-cyano-6-(3-pyridyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil | 1202395-86-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-cyano-6-(3-pyridyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-cyano-4-oxo-6-pyridin-3-yl-2-sulfanylidenepyrimidin-1-yl)oxan-2-yl]methyl acetate
• CAS: 1202395-86-5
• 化学式: C₂₄H₂₄N₄O₁₀S
• 分子量: 560.541
• InChiKey: VWSVFJIVQJZADI-OXUVVOBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  216
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  5-cyano-6-(3-pyridyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil 反应 1.0h， 以18%的产率得到2,2'-anhydro-2-mercapto-6-(3-pyridyl)-1-(3,4,6-tri-O-acetyl-β-D-mannopyranosyl)pyrimidin-5(2H)-one
  参考文献：
  名称：

  A direct synthetic approach to uracil anhydrothionucleoside derivatives

  摘要：

  Direct conversion of peracylated N-1-(beta-D-glucopyranosyl)-2-thiouracil derivatives into the corresponding anhydrothionucleosides has been studied under various conditions including: gas-phase pyrolysis, heating without a solvent, and by heating in a solvent of high boiling point (DPE) in the presence of a base (DABCO) and reaction in a microwave reactor. Heating at 210-220 degrees C was found to give the best yield of a single isomer. The structures of the new anhydrothionucleosides were confirmed by NMR techniques. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.09.006
• 作为产物：
  描述：

  、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 四氯化锡 作用下， 以 乙腈 为溶剂， 生成 5-cyano-6-(3-pyridyl)-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil
  参考文献：
  名称：

  A direct synthetic approach to uracil anhydrothionucleoside derivatives

  摘要：

  Direct conversion of peracylated N-1-(beta-D-glucopyranosyl)-2-thiouracil derivatives into the corresponding anhydrothionucleosides has been studied under various conditions including: gas-phase pyrolysis, heating without a solvent, and by heating in a solvent of high boiling point (DPE) in the presence of a base (DABCO) and reaction in a microwave reactor. Heating at 210-220 degrees C was found to give the best yield of a single isomer. The structures of the new anhydrothionucleosides were confirmed by NMR techniques. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.09.006