Synthesis and structure determination of some glycoconjugates related to mannojirimycin and serine
Conference contribution, 2005
Glycoconjugates of lipids and proteins represent a very important group of organic compounds. Due to their responsibility for recognition in biological events, there is growing interest in the use of synthetic glycopeptides as model compounds.
(5S)-5-Triphenylmethoxymethyl-[5-methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin-2,4-dione(1) was synthesized from methyl 6-O-trityl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose and applying the Bucherer-Bergs reaction. As a minor product, the isomer 3 with 5-R configuration was isolated. Corresponding α-amino acids 5 and 6 were obtained from the above hydantoins by the selective acid hydrolysis of the trityl and isopropylidene groups followed by basic hydrolysis of the hydantoin ring. 2-Oxazolidinone derivate 7 instead of the expected hydantoin was obtained starting from 6-O-unprotected 5-ulose.
The configuration at C-5' atom was unambiguosly established by single-crystal X-ray diffraction analysis of the hydantoin derivative 2.