3-((benzyloxy)methyl)-1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2-hydroxyethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione | 148522-79-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3-((benzyloxy)methyl)-1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2-hydroxyethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 148522-79-6
• 化学式: C₂₅H₃₈N₂O₆Si
• 分子量: 490.672
• InChiKey: QMQWZBBHXFYPKB-BHIFYINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91.92
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-((benzyloxy)methyl)-1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2-hydroxyethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione 在 吡啶 、 甲醇 、 sodium azide 、 2,2,6,6-四甲基哌啶氧化物 、 三正丁胺 、 碘苯二乙酸 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 四丁基磷酸氢铵 、 三苯基膦 、 三氯乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 环己烯 为溶剂， 反应 46.75h， 生成
  参考文献：
  名称：

  Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

  摘要：

  Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 60 position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.042
• 作为产物：
  描述：

  在 9-硼双环[3.3.1]壬烷 、 甲醇 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 25.5h， 以57.2%的产率得到3-((benzyloxy)methyl)-1-((2R,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(2-hydroxyethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Phospho-carboxylic anhydride of a homologated nucleoside leads to primer degradation in the presence of a polymerase

  摘要：

  Starting from thymidine, through a series of key synthetic transformations (e.g., Wittig reaction, hydroboration, Mitsunobu reaction and TEMPO oxidation) a nucleoside homologue bearing a phospho-carboxylic anhydride group at 60 position was synthesized. The potential of polymerases to catalyze amide bond formation was investigated by using a modified primer with an amino group at 3' position and the synthesized phosphoanhydro compound as substrate. Unfortunately, we did not observe the desired product either by gel electrophoresis or mass spectrometry. In contrast, the instability of the phosphoanhydro compound could lead to pyrophosphate formation and thus, to pyrophosphorolysis of the primer rather than to primer extension. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.042