4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine | 1454582-09-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine
• 英文别名: [(2S,3R,4S,5S)-5-(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 1454582-09-2
• 化学式: C₃₃H₂₄BrN₅O₇
• 分子量: 682.487
• InChiKey: AGOUXNNNFPVKRL-YXMNTCDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  168.65
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine 、 双氧水 在 ammonium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以54%的产率得到4-amino-6-bromo-1-((2S,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)1H-pyrrolo[2,3-d]pyrimidine-5-carboxamide
  参考文献：
  名称：

  Selectivity between N-1 and N-7 nucleosides: regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor

  摘要：

  BMK-Y101 is a new pyrrolo[2,3-d]pyrimidine-based potent cdk7 and 9 inhibitor, which is characterized by an intriguing structural feature of N-1 nucleoside, departing from previously reported N-7 nucleoside Cdk inhibitor, xylocydine. Though N-1 nucleosides have appeared in the literature, they have often been considered as kinetic products and thus intermediates of N-7 glycosylation. In the course of the synthetic studies of xylocydine derivatives, we have developed a highly regioselective method to obtain the N-1 nucleoside. The origin of the selectivity is apparently based on the reactivity of the silylated nucleobase and the stability of the resulting N-1 nucleoside. The choice of BSA as a silylating agent was critical in securing the N-1 nucleoside, BMK-Y101. On the other hand, proper selection of reaction conditions promoting transglycosylation provides an efficient route to N-7 nucleosides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.132
• 作为产物：
  描述：

  三氟甲磺酸三甲基硅酯 、 4-氨基-6-溴-7H-吡咯并[2,3-d]嘧啶-5-甲腈 、 1-O-acetyl-2,3,5-tri-O-benzoyl-L-xylofuranose 在 N,O-双三甲硅基乙酰胺 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以37%的产率得到4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-benzoyl-β-L-xylofuranosyl)-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Selectivity between N-1 and N-7 nucleosides: regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor

  摘要：

  BMK-Y101 is a new pyrrolo[2,3-d]pyrimidine-based potent cdk7 and 9 inhibitor, which is characterized by an intriguing structural feature of N-1 nucleoside, departing from previously reported N-7 nucleoside Cdk inhibitor, xylocydine. Though N-1 nucleosides have appeared in the literature, they have often been considered as kinetic products and thus intermediates of N-7 glycosylation. In the course of the synthetic studies of xylocydine derivatives, we have developed a highly regioselective method to obtain the N-1 nucleoside. The origin of the selectivity is apparently based on the reactivity of the silylated nucleobase and the stability of the resulting N-1 nucleoside. The choice of BSA as a silylating agent was critical in securing the N-1 nucleoside, BMK-Y101. On the other hand, proper selection of reaction conditions promoting transglycosylation provides an efficient route to N-7 nucleosides. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.132