781652-93-5Relevant academic research and scientific papers
Synthesis and structure determination of some nonanomerically C-C-linked serine glycoconjugates structurally related to mannojirimycin
Mi?ová, Júlia,Steiner, Bohumil,Koó?, Miroslav,Langer, Vratislav,Gyepesová, Dalma
, p. 2187 - 2195 (2004)
The Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-α-D-lyxo- hexofuranosid-5-ulose gave (4′S)-4′-carbamoyl-4′-[methyl (4R)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-oxazolidin-2′- one instead of expected hydantoins. A mixture of hydantoins - (5′R)-triphenylmethoxymethyl-5′-[methyl (4R)-2,3-O-isopropylidene- β-l-erythrofuranosid-4-C-yl]-imidazolidin-2′,4′-dione and (5′S)-triphenylmethoxymethyl-5′-[methyl (4R)-2,3-O-isopropylidene- β-L-erythrofuranosid-4-C-yl]-imidazolidin-2′,4′-dione was obtained from the 5-ulose having protected primary OH group at C-6. The 4′-S configuration of 2 as well as 5′-S configuration of (5′S)-hydroxymethyl-5′-[methyl (4R)-2,3-O-isopropylidene-β-L- erythrofuranosid-4-C-yl]-imidazolidin-2′,4′-dione (9) was confirmed by X-ray crystallography. Corresponding α-amino acid-methyl (5S)-5-amino-5-C-carboxy-5-deoxy-α-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4R)-β-L-erythrofuranosid-4-C-yl]-L-serine) (11) was obtained from the hydantoin 9 by acid hydrolysis of the isopropylidene and trityl groups followed by basic hydrolysis of the hydantoin ring. Analogous derivatives with 5-R configuration, formed in a minority, were also isolated and characterised.
