Preparation and structure determination of two sugar amino acids via corresponding hydantoin derivatives

(4 R)-2,3- O-Isopropylidene-methylspiro[4,6-dideoxy-α- l- lyxo-hexopyranosid-4,5′-imidazolidin]-2′,4′-dione and (4 R)-2,3- O-isopropylidene-methylspiro[4,6-dideoxy-β- d- ribo-hexopyranosid-4,5′-imidazolidin]-2′,4′-dione were prepared under various reaction conditions starting from methyl 6-deoxy-2,3- O-isopropylidene-α- l- lyxo-hexopyranosid-4-ulose. Corresponding α-amino acids methyl (4 R)-4-amino-4- C-carboxy-4,6-dideoxy-α- l- lyxo-hexopyranoside and methyl (4 R)-4-amino-4- C-carboxy-4,6-dideoxy-β- d- ribo-hexopyranoside were obtained from the above hydantoins by selective acid hydrolysis of the isopropylidene group, followed by basic hydrolysis of the hydantoin ring. The crystal structures of both hydantoin derivatives are also presented.