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Synthesis and X-ray structure of a C5–C4-linked glucofuranose–oxazolidin-2-one

Bohumil Steiner ; Vratislav Langer (Institutionen för kemi- och bioteknik, Oorganisk miljökemi) ; Miroslav Koos
Carbohydrate Research (0008-6215). Vol. 344 (2009), 15, p. 2079-2082.
[Artikel, refereegranskad vetenskaplig]

The formation of (4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene-β-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-α-D-glucofuranose or 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose under Bucherer–Bergs reaction conditions is reported. Single crystal X-ray diffraction data revealed that 3T4 is the prefered conformation for the furanose ring, while E2 and 2T1 conformations are adopted by the 1,3-dioxolane and 2-oxazolidinone five-membered rings, respectively.

Nyckelord: oxazolidin-2-one, Bucherer-Bergs reaction, glucofuranose, X-ray diffraction, conformation, glycoconjugate

Denna post skapades 2009-09-22. Senast ändrad 2013-10-29.
CPL Pubid: 98488


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