Synthesis and X-ray structure of a C5-C4-linked glucofuranose-oxazolidin-2-one.
The formation of (4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene-beta-l-threofuranos-4-C-yl]-oxazolidin-2-one instead of expected imidazolidin-2,4-dione (hydantoin) derivative from 5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-alpha-d-glucofuranose or 3-O-benzyl-1,2-O-isopropylidene-alpha-d-xylo-hexofuranos-5-ulose under Bucherer-Bergs reaction conditions is reported. Single crystal X-ray diffraction data revealed that (3)T(4) is the prefered conformation for the furanose ring, while E(2) and (2)T(1) conformations are adopted by the 1,3-dioxolane and 2-oxazolidinone five-membered rings, respectively.
Steiner
Bohumil
B
Institute of Chemistry, Centre of Excelence GLYCOMED, Slovak Academy of Sciences, Bratislava, Slovakia.
Langer
Vratislav
V
Koós
Miroslav
M
D006001:Glycoconjugates / Q000737:chemistry*; D015394:Molecular Structure; D014961:X-Ray Diffraction
D006001:Glycoconjugates