Stereoselective synthesis of chiral furan amino acid analogues of D- and L-serine from D-sugars

Abstract

The synthesis of chiral furan amino acid analogues of D - and L -serine is reported. The developed methodology starting from D -xylose affords the corresponding amino acid derivative analogue of D -serine enantiomerically pure. Starting from D -arabinose, the corresponding analogue of L -serine was isolated in 92.3% enantio- meric purity. The analogue of D -serine was transformed into a stable Fmoc activated derivative ready to be incorporated into peptides.