9-(2,3,5-tri-O-benzyl-4-thio-β-D-ribofuranosyl)-adenine | 161424-53-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 9-(2,3,5-tri-O-benzyl-4-thio-β-D-ribofuranosyl)-adenine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)thiolan-2-yl]purin-6-amine
• CAS: 161424-53-9
• 化学式: C₃₁H₃₁N₅O₃S
• 分子量: 553.685
• InChiKey: SVFCDKKKWWDFHW-QWOIFIOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.31
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-(2,3,5-tri-O-benzyl-4-thio-β-D-ribofuranosyl)-adenine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以70%的产率得到2-(6-氨基嘌呤-9-基)-5-(羟基甲基)四氢噻吩-3,4-二醇
  参考文献：
  名称：

  A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

  摘要：

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

  DOI：

  10.1080/15257779408013205
• 作为产物：
  描述：

  2,3,5-tri-O-benzyl-4-O-p-nitrobenzoyl-L-lyxose dithiobenzylacetal 在 吡啶 、 TMSTf 、 4 A molecular sieve 、 mercury(II) diacetate 、 四丁基碘化铵 、 potassium carbonate 、 甲基磺酰氯 、 barium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 49.0h， 生成 9-(2,3,5-tri-O-benzyl-4-thio-β-D-ribofuranosyl)-adenine
  参考文献：
  名称：

  A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

  摘要：

  A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

  DOI：

  10.1080/15257779408013205