5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-2-pyrimidin-4(1H)-one | 1202395-88-7

• 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-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-2-pyrimidin-4(1H)-one
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[5-cyano-6-(4-methoxyphenyl)-4-oxo-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpyrimidin-1-yl]oxan-2-yl]methyl acetate
• CAS: 1202395-88-7
• 化学式: C₄₀H₄₅N₃O₂₀S
• 分子量: 919.871
• InChiKey: FPXGZKWHMJECRC-MGMZGQFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  320
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-2-pyrimidin-4(1H)-one 反应 0.5h， 以16%的产率得到2,2'-anhydro-2-mercapto-6-p-methoxyphenyl-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：

  5-cyano-4-oxo-6-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 氢氧化钾 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 以50%的产率得到5-cyano-6-p-methoxyphenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthio)-2-pyrimidin-4(1H)-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