Regioselective synthesis of C-nucleosides by 1,3-dipolar cycloaddition of arylnitrile oxides to 5,6-dideoxy-1,2- O-iso-propylidene-α- d- xylo-hex-5-enofuranose

Abstract

The synthesis of 3-aryl-5-(1,2- O-isopropylidene-α- d- xylo-tetrofuranos-4-yl)-2-isoxazoline ( 3) from arylnitrile oxides and 5,6-dideoxy-1,2- O-isopropylidene-α- d- xylo-hex-5-enofuranose ( 1) is described. The 1,3-dipolar cycloaddition reactions give mainly anti-adducts (⩾95% π-facial stereoselectivity).