1-(2',3',5'-tri-O-acetyl-β-D-xylopyranosyl)-2-(2'',3'',5''-tri-O-acetyl-β-D-xylopyranosylthio)-5-cyano-6-(2-naphthyl)-pyrimidin-4(1H)-one | 289906-63-4

• 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)-2-(2'',3'',5''-tri-O-acetyl-β-D-xylopyranosylthio)-5-cyano-6-(2-naphthyl)-pyrimidin-4(1H)-one
• 英文别名: [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[5-cyano-6-naphthalen-2-yl-4-oxo-2-[(2S,3R,4S,5R)-3,4,5-triacetyloxyoxan-2-yl]sulfanylpyrimidin-1-yl]oxan-3-yl] acetate
• CAS: 289906-63-4
• 化学式: C₃₇H₃₇N₃O₁₅S
• 分子量: 795.778
• InChiKey: PMMRTCRDBSCNGL-JQXKABPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  258
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  1-(2',3',5'-tri-O-acetyl-β-D-xylopyranosyl)-2-(2'',3'',5''-tri-O-acetyl-β-D-xylopyranosylthio)-5-cyano-6-(2-naphthyl)-pyrimidin-4(1H)-one 在 氨 作用下， 以 甲醇 为溶剂， 生成 5-cyano-6-(2-naphthyl)-(1-β-D-xylopyranosyl)-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：

  5-cyano-6-(2-naphthyl)-2-thiouracil 、 2,3,4-三-O-乙酰基-α-D-木吡喃糖苷溴 在 氢氧化钾 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 以35%的产率得到1-(2',3',5'-tri-O-acetyl-β-D-xylopyranosyl)-2-(2'',3'',5''-tri-O-acetyl-β-D-xylopyranosylthio)-5-cyano-6-(2-naphthyl)-pyrimidin-4(1H)-one
  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