A synthesis of abequose (3,6-Dideoxy-D-xylo-hexose)

Abstract

The S-methyl 3-O-dithiocarbonates of 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose and ?gulofuranose have been prepared and subsequently reduced with tributylstannane to 3-deoxy-1,2:5,6-di-O-isopropylidene-μ- D-xylo-hexofuranose. Partial hydrolysis of this compound led to the 5,6-diolwhich was deoxygenated at C 6 to form 3,6-dideoxy-1,2-O- isopropylidene-α-D-xylo-hexofuranose, and subsequently abequose on acid hydrolysis. A rationale has been proposed for the variations in hydrolysis of di-O-isopropylidene-α-D-hexofuranoses and derivatives to their 5,6-diols.