Cycloaddition of nitrile oxides to 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-d-ribo-hex-5-enofuranose

Autor: Blake, Alexander J., Gould, Robert O., McGhie, Karen E., Paton, R.Michael, Reed, David, Sadler, Ian H., Young, Anne A.
Zdroj: Carbohydrate Research; September 1992, Vol. 216 Issue: 1 p461-473, 13p
Abstrakt: Benzonitrile oxide and ethoxycarbonylformonitrile oxide cyclo-added to the title compound to afford a mixture of 3-substituted (phenyl or ethoxycarbonyl) (5R- (6) and (5S)-5-(3-O-benzyl-1,2-O-isopropylidene-α-d-ribo-tetrofuranos-4-yl)-2-isoxazoline (7). The π-facial selectivity of the reactions was low (∼1:1) compared with that (9:1) for the corresponding d-xyloisomer of the title compound, which yielded the d-xyloisomers (2and 3, respectively) of 6and 7. The structures of the 3-phenyl derivatives 2aand 6awere determined by X-ray crystallography.
Databáze: Supplemental Index