6-<<4-benzyl>thio>-9-(β-D-ribofuranosyl)purine | 143330-48-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-<<4-benzyl>thio>-9-(β-D-ribofuranosyl)purine
• 英文别名: 6-({4-[N-(propylsulfonyl)amino]benzyl}thio)-9-(β-D-ribofuranosyl)purine；N-[4-[[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]sulfanylmethyl]phenyl]propane-1-sulfonamide
• CAS: 143330-48-7
• 化学式: C₂₀H₂₅N₅O₆S₂
• 分子量: 495.58
• InChiKey: SQRMPHVKFZCTAZ-WVSUBDOOSA-N

物化性质

• 沸点：
  791.8±70.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  193
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  对氨基苯甲醇 在 吡啶 、 4-二甲氨基吡啶 、 氨 、 碳酸氢钠 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 43.33h， 生成 6-<<4-benzyl>thio>-9-(β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Photochemistry of nucleoside transport inhibitor 6-S-benzylated thiopurine ribonucleosides. Implications for a new class of photoaffinity labels

  摘要：

  Photochemistry of the nucleoside transport inhibitor 6-[(4-nitrobenzyl)thio]-9-(beta-D-ribofuranosyl)purine (NBMPR, 1) yielded products from the initial homolytic cleavage of the benzyl-sulfur bond. Photoreduction of the nitro group also occurred to a minor extent. The quantum yield for the disappearance of 1 was approximately 0.04. Several photoproducts and secondary photoproducts were identified and confirmed by synthesis. Irradiation of 6-(benzylthio)-9-(beta-D-ribofuranosyl)purine (BMPR, 3) also resulted in the formation of products from benzyl-sulfur cleavage with a quantum yield of approximately 0.01.

  DOI：

  10.1021/jo00048a034

文献信息

• Photochemistry of nucleoside transport inhibitor 6-S-benzylated thiopurine ribonucleosides. Implications for a new class of photoaffinity labels
  作者：Steven A. Fleming、David B. Rawlins、Vicente Samano、Morris J. Robins

  DOI：10.1021/jo00048a034

  日期：1992.10

  Photochemistry of the nucleoside transport inhibitor 6-[(4-nitrobenzyl)thio]-9-(beta-D-ribofuranosyl)purine (NBMPR, 1) yielded products from the initial homolytic cleavage of the benzyl-sulfur bond. Photoreduction of the nitro group also occurred to a minor extent. The quantum yield for the disappearance of 1 was approximately 0.04. Several photoproducts and secondary photoproducts were identified and confirmed by synthesis. Irradiation of 6-(benzylthio)-9-(beta-D-ribofuranosyl)purine (BMPR, 3) also resulted in the formation of products from benzyl-sulfur cleavage with a quantum yield of approximately 0.01.