2',3',5'-Tri-O-acetyl-6-bromotoyocamycin | 74112-93-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 2',3',5'-Tri-O-acetyl-6-bromotoyocamycin
• 英文别名: 4-amino-6-bromo-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine；4-amino-6-bromo-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-7-yl)oxolan-2-yl]methyl acetate
• CAS: 74112-93-9
• 化学式: C₁₈H₁₈BrN₅O₇
• 分子量: 496.274
• InChiKey: RXTPLBRSCAGVDS-XWXWGSFUSA-N

物化性质

• 沸点：
  691.0±55.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-Tri-O-acetyl-6-bromotoyocamycin 在 palladium on activated charcoal 吡啶 、 甲醇 、 ammonium hydroxide 、 Dowex-50 、 氢气 、 双氧水 、 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 桑霉素
  参考文献：
  名称：

  Synthesis of 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin and Some Related Derivatives

  摘要：

  A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azidod-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

  DOI：

  10.1080/15257779508010707
• 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 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

文献信息

• Reductive debromination of some purine and purine-like nucleosides
  作者：Fung-Lung Chung、Robert A. Earl、Leroy B. Townsend

  DOI：10.1021/jo01308a025

  日期：1980.9