1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-cyano-6-phenyl-2-thiouracil | 317833-73-1

• 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-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-cyano-6-phenyl-2-thiouracil
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(5-cyano-4-oxo-6-phenyl-2-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 317833-73-1
• 化学式: C₂₂H₂₁N₃O₈S
• 分子量: 487.49
• InChiKey: JYUCVXKYQYZBEH-XLBJILASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-cyano-6-phenyl-2-thiouracil 在 氨 作用下， 以 甲醇 为溶剂， 以86%的产率得到5-cyano-6-phenyl-1-(β-D-ribofuranosyl)-2-thiocytosine
  参考文献：
  名称：

  A Facile Synthesis of 6-Aryl-5-cyano-1-(β-d-pyranosyl or β-d-furanosyl)-2-thiocytosines

  摘要：

  The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-alpha -D-pyranosyl bromide produces a mixture of N1-(beta -D-pyranosyl)-2-thiouracil and its N1,S-2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-pcracetyl-beta -D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the P-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to beta -D-ribosyl nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00807-3
• 作为产物：
  描述：

  1,2,3,4-四氢-4-氧代-6-苯基-2-硫代-5-嘧啶甲腈 在 硫酸氢铵 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 1-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-5-cyano-6-phenyl-2-thiouracil
  参考文献：
  名称：

  A Facile Synthesis of 6-Aryl-5-cyano-1-(β-d-pyranosyl or β-d-furanosyl)-2-thiocytosines

  摘要：

  The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-alpha -D-pyranosyl bromide produces a mixture of N1-(beta -D-pyranosyl)-2-thiouracil and its N1,S-2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-pcracetyl-beta -D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the P-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to beta -D-ribosyl nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00807-3