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.
Design and synthesis of 3′,5′-ansa-adenosines as potential Hsp90 inhibitors
摘要:
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.
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.
Design and synthesis of 3′,5′-ansa-adenosines as potential Hsp90 inhibitors
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.