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

Bohumil Steiner; Vratislav Langer; Miroslav Koós

doi:10.1016/j.carres.2009.06.031

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

Carbohydr Res. 2009 Oct 12;344(15):2079-82. doi: 10.1016/j.carres.2009.06.031. Epub 2009 Jun 26.

Authors

Bohumil Steiner¹, Vratislav Langer, Miroslav Koós

Affiliation

¹ Institute of Chemistry, Centre of Excelence GLYCOMED, Slovak Academy of Sciences, Bratislava, Slovakia.

PMID: 19683708
DOI: 10.1016/j.carres.2009.06.031

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Glycoconjugates / chemistry*
Molecular Structure
X-Ray Diffraction

Substances

Glycoconjugates