164665-98-9Relevant academic research and scientific papers
Glucofuranose analogues of hydantocidin
Brandstetter, Tilmann W.,De La Fuente, Carmen,Kim, Yong-ha,Johnson, Louise N.,Crook, Sarah,De Q. Lilley, Paul M.,Watkin, David J.,Tsitsanou, Katerina E.,Zographos, Spyros E.,Chrysina, Enangelia D.,Oikonomakos, Nikos G.,Fleet, George W.J.
, p. 10721 - 10736 (2007/10/03)
Epimeric spirohydantoins of glucofuranose, analogues of hydantocidin, are readily prepared from glucoheptonolactone. No rearrangement of spirohydantoins of glucofuranose to pyranose isomers was observed; a novel rearrangement was observed of a glucofuranose spirohydantoin to an isomeric oxazolidinone, (3aR,4'R,5S,6S,6aR)-5-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-6-hydroxy -3a-N-phenylcarboxamido-tetrahydrofuro[2.3-d]-1,2-oxazolidine-2-one, the structure of which was established by X-ray crystallographic analysis. The X-ray crystal structure of (1'R,2R,3R,4R,5R)-6,8-diaza-3,4-dihydroxy-2-(1',2'-dihydroxyethyl)-1-o xa-8-N-phenyl spiro[4.4]nonane-7,9-dione is reported.
SPIROHYDANTOINS OF GLUCOFURANOSE: ANALOGUES OF HYDANTOCIDIN
Brandstetter, Tilmann W.,Kim, Yong-ha,Son, Jong Chan,Taylor, Helen M.,Lilley, Paul M. de Q.,et al.
, p. 2149 - 2152 (2007/10/02)
Routes from both γ- and δ-glucoheptonolactones to spirohydantoins of glucofuranose are described, affording further analogues of hydantocidin.It may be that the glucofuranose isomers are more stable than the glucopyranose forms.
