360577-31-7Relevant articles and documents
Synthesis and structure determination of some sugar amino acids related to alanine and 6-deoxymannojirimycin
Koos, Miroslav,Steiner, Bohumil,Micova, Julia,Langer, Vratislav,Durik, Marian,Gyepesova, Dalma
, p. 351 - 361 (2007/10/03)
(5′R)-5′-Methyl-5′-[methyl (4S)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-imidazolidin- 2′,4′-dione was synthesised starting from methyl 6-deoxy-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-α-D-lyxo-hexofuranoside (alternative name: 2-[methyl (4S)-2,3-O-isopropylidene-β-L-erythrofuranosid-4-C-yl]-D-alanine) was obtained from the above hydantoin by acid hydrolysis of the isopropylidene group followed by basic hydrolysis of the hydantoin ring. Total deprotection afforded 5-C-carboxy-6-deoxymannojirimycin. Analogously, methyl (5S)-5-amino-5-C-carboxy-5,6-dideoxy-α-L-lyxo-hexofuranoside and 5-C-carboxy-6-deoxy-L-mannojirimycin were prepared from the corresponding (5′S)-5′-methyl-5′-[methyl (4R)-2,3-O-isopropylidene-β-D-erythrofuranosid-4-C-yl]-imidazolidin- 2′,4′-dione starting from methyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexofuranosid-5-ulose.