6-N,N-dibenzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl)adenine | 188486-27-3

• 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: 6-N,N-dibenzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl)adenine
• 英文别名: N-benzoyl-N-[9-[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxooxolan-2-yl]purin-6-yl]benzamide
• CAS: 188486-27-3
• 化学式: C₃₆H₄₇N₅O₆Si₂
• 分子量: 701.97
• InChiKey: HXUJBZYEBUYCEV-DWRBMJLUSA-N

物化性质

• 沸点：
  737.5±70.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  49.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  125.74
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-N,N-dibenzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl)adenine 在 吡啶 、 potassium permanganate 、 三氯化铝 、 phosphate buffer 、 cerium(III) chloride 、 四丁基氟化铵 、 臭氧 、 二氯磷酸苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 15.0h， 生成 6-N-benzoyl-9-(2-O-acetyl-3,5-O-isopropylidene-3-C-phenylselenocarbonyl-β-D-xylofuranosyl)adenine
  参考文献：
  名称：

  Studies on the Mechanism of Ribonucleotide Reductases

  摘要：

  Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 . 10(6) s(-1) in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 10(3) times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.

  DOI：

  10.1021/ja962974q
• 作为产物：
  描述：

  6-N,N-dibenzoyl-2',5'-di-O-(tert-butyldimethylsilyl)adenosine 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以99%的产率得到6-N,N-dibenzoyl-9-(2,5-di-O-(tert-butyldimethylsilyl)-β-D-erythro-pentofuran-3-ulosyl)adenine
  参考文献：
  名称：

  Studies on the Mechanism of Ribonucleotide Reductases

  摘要：

  Ribonucleotide reductases are enzymes that catalyze the conversion of ribonucleotides to 2'-deoxyribonucleotides. This important reaction is initiated by the generation of a C-3' nucleotide radical and subsequent loss of the 2'-hydroxyl group. In order to model certain steps in this mechanism, selenol ester 23 was prepared and photolyzed providing the first selective chemical access to the 3'-adenosyl radical. From product analysis it could be shown that elimination of the 2'-OH function readily takes place under general base catalysis. The rate coefficient for this reaction was determined by competition kinetics to be 1.5 . 10(6) s(-1) in the presence of 1 M triethylammonium acetate buffer at pH 7. Without catalyst the elimination rate is about 10(3) times slower. It can be concluded that a similar mechanism is also feasible for the key steps of the enzyme catalyzed reaction.

  DOI：

  10.1021/ja962974q