Characterisation and X-ray crystallography of products from the Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside
Journal article, 2003

Methyl 2,3-O-isopropylidene-α-D-mannofuranosidurononitrile [alternative name: methyl (5R)-5-C-cyano-2,3-O-isopropylidene-α-D-lyxofuranoside] (2), methyl 2,3-O-isopropylidene-α-D-mannofuranosiduronamide [methyl (5S)-5-C-carbamoyl-2,3-O-isopropylidene-α-D-lyxofuranoside; methyl (5S)-2,3-O-isopropylidene-α-D-lyxo-hexofuranosiduronamide] (3), methyl 2,3-O-isopropylidene-α-D-mannofuranosiduronic acid [methyl (5S)-2,3-O-isopropylidene-α-D-lyxo-hexofuranosiduronic acid] (4), methyl 5-deoxy-2,3-O-isopropylidene-5-ureido-β-L-gulofuranosiduronamide [methyl (5R)-5-deoxy-2,3-O-isopropylidene-5-ureido-α-D-lyxo-hexofuranosiduronamide (5), and (4S,5S,6R)-5,6-dihydro-6-hydroxy-4,5-isopropylidenedioxy-4H-pyrido[2,1-e]imidazolidine-2',4'-dione [IUPAC name: (3aS,4R,8aS)-4-hydroxy-2,2-dimethyl-3a,8a-dihydro-4H-1,3-dioxa-4a,6-diaza-s-indacene-5,7-dione] (6), instead of the expected hydantoin derivative, were obtained from the Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside (1). The structure of 6 was deduced from NMR and mass spectral data and confirmed by X-ray crystallography. The configuration at C-5 in 2-5 was confirmed by establishing the 5S configuration of 3 by X-ray crystallography. Conformations of the six- and five-membered rings in 3 and 6 are also discussed.

Pyrido[2

X-ray crystallography

Pentodialdo-1

4-furanoside

1-e]imidazolidine

Conformation

Furanosiduronamide

Bucherer–Bergs reaction

Author

Julia Micova

Slovak Academy of Sciences

Bohumil Steiner

Slovak Academy of Sciences

Miroslav Koos

Slovak Academy of Sciences

Vratislav Langer

Chalmers, Department of Environmental Inorganic Chemistry

Dalma Gyepesova

Slovak Academy of Sciences

Carbohydrate Research

0008-6215 (ISSN)

Vol. 338 19 1917-1924

Subject Categories

Chemical Sciences

DOI

10.1016/S0008-6215(03)00307-0

More information

Created

10/6/2017