(3S,4S,5R)-4-(6-aminopurin-9-yl)-5-(dimethoxymethyl)oxolan-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (3S,4S,5R)-4-(6-aminopurin-9-yl)-5-(dimethoxymethyl)oxolan-3-ol
• 化学式: C₁₂H₁₇N₅O₄
• 分子量: 295.298
• InChiKey: JPIVYOQPBJQSSH-BWVDBABLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,5-Anhydro-D-xylose dimethyl acetal 3-(4-methylbenzenesulfonate) 在 18-冠醚-6 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 69.0h， 生成 (3S,4S,5R)-4-(6-aminopurin-9-yl)-5-(dimethoxymethyl)oxolan-3-ol
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x

文献信息

• Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines
  作者：Hong-Wu Yu、Liang-Ren Zhang、Ji-Chang Zhou、Ling-Tai Ma、Li-He Zhang

  DOI：10.1016/0968-0896(96)00048-x

  日期：1996.4

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd