An improved aldehyde linker for the solid phase synthesis of hindered amides

MJ Liley, T Johnson, SE Gibson

Index: Liley, Mark J.; Johnson, Tony; Gibson, Susan E. Journal of Organic Chemistry, 2006 , vol. 71, # 4 p. 1322 - 1329

Full Text: HTML

Citation Number: 16

Abstract

A novel aldehyde dual-linker system has been developed for the solid phase synthesis of sterically hindered amides. The linker [5-(4-formyl-3-hydroxyphenoxy) pentanoic acid] exploits an intramolecular oxygen-nitrogen acyl transfer mechanism to prepare compounds that are unattainable with current commercially available linkers. A dual linker system, exploiting the hyper-acid labile Sieber amide linker as part of the construct, enabled the ...