1-(β-D-glucopyranosyl)-5-cyano-6-(p-tolyl)-2-thiocytosine

• 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-(β-D-glucopyranosyl)-5-cyano-6-(p-tolyl)-2-thiocytosine
• 英文别名: 5-cyano-1-(β-D-glucopyranosyl)-6-(4-tolyl)-2-thiocytosine；4-amino-6-(4-methylphenyl)-2-sulfanylidene-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyrimidine-5-carbonitrile
• 化学式: C₁₈H₂₀N₄O₅S
• 分子量: 404.447
• InChiKey: QJCKFRBXOOFYGK-OQAPJDJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  188
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-oxo-2-thioxo-6-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 在 氢氧化钾 、 氨 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 1-(β-D-glucopyranosyl)-5-cyano-6-(p-tolyl)-2-thiocytosine
  参考文献：
  名称：

  The first direct ammonolysis of 2-thiouracil nucleosides to 2-thiocytosine nucleosides

  摘要：

  Sugar-peracetylated 1-(beta-D-glucopyranosyl)-, 1-(beta-D-galactopyranosyl)-, and 1-(beta-D-xylopyranosyl)-6-aryl-5-cyano-2-thiouracils 2-4 and the corresponding 1-pyranosyl-2-(pyranosylthio)pyrimidines 5-7 undergo efficient ammonolysis (NH3/MeOH, 0-->23 degrees C, 16 h) to give the corresponding 1-(beta-D-pyranosyl)-6-aryl-5-cyano-2-thiocytosines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00712-7

文献信息

• A Facile Synthesis of 6-Aryl-5-cyano-1-(β-d-pyranosyl or β-d-furanosyl)-2-thiocytosines
  作者：Ibrahim M Abdou、Lucjan Strekowski

  DOI：10.1016/s0040-4020(00)00807-3

  日期：2000.10

  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.