4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine | 1454582-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-1-yl)oxolan-2-yl]methyl acetate
• CAS: 1454582-12-7
• 化学式: C₁₈H₁₈BrN₅O₇
• 分子量: 496.274
• InChiKey: RWUHBIMPCRFQJS-XWXWGSFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 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-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 以 乙腈 为溶剂， 以59%的产率得到2',3',5'-Tri-O-acetyl-6-bromotoyocamycin
  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：

  2-氨基-5-溴-1H-吡咯-3,4-二甲腈 在 叔丁基二甲基氯硅烷 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 4-amino-6-bromo-5-cyano-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)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