1-(2',3',5'-tri-O-acetyl-β-D-xylopyranosyl)-5-cyano-6-(2-naphthyl)-2-thiouracil | 289906-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2',3',5'-tri-O-acetyl-β-D-xylopyranosyl)-5-cyano-6-(2-naphthyl)-2-thiouracil
• 英文别名: [(3R,4S,5R,6R)-4,5-diacetyloxy-6-(5-cyano-6-naphthalen-2-yl-4-oxo-2-sulfanylidenepyrimidin-1-yl)oxan-3-yl] acetate
• CAS: 289906-62-3
• 化学式: C₂₆H₂₃N₃O₈S
• 分子量: 537.55
• InChiKey: MIKSIAWDJAEVSC-JVICHNFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 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-xylopyranosyl)-5-cyano-6-(2-naphthyl)-2-thiouracil 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以84%的产率得到5-cyano-6-(2-naphthyl)-(1-β-D-xylopyranosyl)-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
• 作为产物：
  描述：

  5-cyano-6-(2-naphthyl)-2-thiouracil 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-xylopyranosyl)-5-cyano-6-(2-naphthyl)-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