A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks

Molecules

Trinidad Velasco-Torrijos¹  Lorna Abbey¹ 

关键词: synthetic glycolipids;    glycosylated amino acids;    glycomimetics;    aspartic acid;    racemization;   

DOI  :  10.3390/molecules171011346

来源: mdpi

【 摘 要 】

L-Aspartic acid building blocks bearing galactosyl moieties were used to synthesise glycolipid mimetics of variable hydrocarbon chain length. The glycolipids were readily prepared through amide bond formation using the TBTU/HOBt coupling methodology. It was observed that, under these conditions, activation of the α-carboxylic acid of the intermediates led to near complete racemisation of the chiral centre if the reaction was carried out in the presence of a base such as triethylamine. The enantiomerically pure glycolipids were obtained after careful consideration of the synthetic sequence and by performing the coupling reactions in the absence of base.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.