Peer-Reviewed Journal Details
Mandatory Fields
Velasco-Torrijos, T;Abbey, L;O'Flaherty, R
2012
October
Molecules
A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks
Published
3 ()
Optional Fields
CARBOHYDRATE GLYCOMIMETICS PEPTIDES DRUGS
17
11346
11362
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 alpha-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.
BASEL
1420-3049
10.3390/molecules171011346
Grant Details