Stereoselective Synthesis of Chiral Furan Amino Acid Analogues of d- and l-Serine from d-Sugars

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% enantiomeric purity. The analogue of d-serine was transformed into a stable Fmoc activated derivative ready to be incorporated into peptides.