(4E,6R,8R,9R,10S,13Z)-8-(6-aminopurin-9-yl)-9-hydroxy-17-methoxy-7,11-dioxa-2-azatricyclo[14.3.1.06,10]icosa-1(19),4,13,16-tetraene-3,18,20-trione | 1207189-99-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (4E,6R,8R,9R,10S,13Z)-8-(6-aminopurin-9-yl)-9-hydroxy-17-methoxy-7,11-dioxa-2-azatricyclo[14.3.1.06,10]icosa-1(19),4,13,16-tetraene-3,18,20-trione
• CAS: 1207189-99-8
• 化学式: C₂₃H₂₂N₆O₇
• 分子量: 494.464
• InChiKey: BGXKGXWTAFQBLW-LDYNPVPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (4E,6R,8R,9R,10S,13Z)-9-hydroxy-17-methoxy-18,20-bis(methoxymethoxy)-8-[6-(tritylamino)purin-9-yl]-7,11-dioxa-2-azatricyclo[14.3.1.06,10]icosa-1(19),4,13,16(20),17-pentaen-3-one 在 三乙基硅烷 、 palladium 10% on activated carbon 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (4E,6R,8R,9R,10S,13Z)-8-(6-aminopurin-9-yl)-9-hydroxy-17-methoxy-7,11-dioxa-2-azatricyclo[14.3.1.06,10]icosa-1(19),4,13,16-tetraene-3,18,20-trione
  参考文献：
  名称：

  Development of the Carboxamide Protecting Group, 4-(tert-Butyldimethylsiloxy)-2-methoxybenzyl

  摘要：

  The new carboxamide protecting group, 4-(tert-butyldimethylsiloxy)-2-methoxybenzyl (SiMB), has been developed. While this SiMB group can be removed using mild basic desilylation methods, it can also be deprotected under strongly acidic or oxidative conditions. An application of this group to simple carboxamide groups, as well as to more complex and acid-sensitive adenosine derivatives containing a cyclophane scaffold, was also demonstrated.

  DOI：

  10.1021/jo201495w

文献信息

• Design and synthesis of 3′,5′-ansa-adenosines as potential Hsp90 inhibitors
  作者：Kazuhiro Muranaka、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1016/j.tetlet.2009.06.094

  日期：2009.9

  3',5'-Ansa-adenosine derivatives, rationally designed as an Hsp90 inhibitor by extracting and fusing a natural product, geldanamycin, and a natural substrate, ATP, were efficiently synthesized by the ring-closing metathesis assisted by the 2,4-dimethoxybenzyl group. This simpler scaffold design provides a practical synthesis of a set of analogs and demonstrates synthetic innovation. (C) 2009 Elsevier Ltd. All rights reserved.