Journal of Organic Chemistry 2003-12-12

Facile synthesis of alpha,alpha-diisobutylglycine and anchoring its derivatives onto PAL-PEG-PS resin.

Yanwen Fu, Marcus A Etienne, Robert P Hammer

Index: J. Org. Chem. 68(25) , 9854-7, (2003)

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Abstract

alpha,alpha-Diisobutylglycine has been synthesized using a Pd-mediated dialkylation of ethyl nitroacetate as a key first step. The free alphaalphaAA is N(alpha)-protected and has been applied to the assembly of conformationally constrained peptide analogues. Mixed anhydrides from BOP-Cl and Fmoc-alphaalphaAA-OH are used for anchoring alphaalphaAAs onto a trialkoxybenzyl linker on PEG-PS grafted support, upon which a beta-strand mimic with difficult sequence is assembled in a superior quality.