600736-96-7Relevant academic research and scientific papers
Some non-anomerically C-C-linked carbohydrate amino acids related to leucine - Synthesis and structure determination
Steiner, Bohumil,Micova, Julia,Koos, Miroslav,Langer, Vratislav,Gyepesova, Dalma
, p. 1349 - 1357 (2003)
(5′R)-5′-Isobutyl-5′-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin- 2′,4′-dione was synthesised starting from methyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside via methyl 6-deoxy-6-isopropyl-2,3-O-isopropylidene-α-D-lyxo-hexofuranosid-5-ulose applying the Bucherer-Bergs reaction. Its 5′-R configuration was confirmed by X-ray crystallography. Corresponding α-amino acid-methyl (5R)-5-amino-5-C-carboxy-5,6-dideoxy-6-isopropyl-α-D-lyxo- hexofuranoside (alternative name: 2-[methyl (4R)-β-L-erythrofuranosid-4-C-yl]-D-leucine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5S configuration, formed in a minority, were also isolated and characterised.
