Carbon-branched δ-tetrahydrofuran sugar amino acids (SAAs) as dipeptide isostere scaffolds

The synthesis of the first branched sugar amino acid (SAA) scaffolds [methyl (3R,4R,5R)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate and methyl (3R,4R,5S)-5-azidomethyl-3,4-dihydroxy-tetrahydrofuran-3-carboxylate] by all efficient intramolecular displacement of a highly hindered neopentyl triflate allows access to enantiopure THF derivatives which have carbon substituents. (C) 2008 Elsevier Ltd. All rights reserved.