Additional reactions of sugar oximes, nitrite oxides and hydroximolactones

Abstract

Reaction of sugar oximes with dimethyl acetylenedicarboxylate gave chiral isoxazolines bearing a sugar moiety. Sugar nitrite oxides reacted with 1,3-dipolarophiles to afford the corresponding isoxazoles bearing a sugar moiety. Sugar hydroximolactones underwent a tandem Michael addition-1,3-dipolar cycloaddition by reaction with Michael acceptors to give the corresponding spiro sugar isoxazolidines. An X-ray crystallographic structure determination of (3S,5R,7R,8R,9R)-3-acetyl-8,9-isopropylidenedioxy-l-(3-oxobutyl)-7-trityloxymethyl-2,6-dioxa-1-azaspiro[4.4]nonane has been performed.