4-Octulose Derivatives; Part 8:1Highly Stereocontrolled Synthesis of 2-Deoxy-4-octulosononitriles by Reformatsky-Type Reaction

2-Deoxy-4,5:6,7-di-O-isopropylidene-β-D-manno-oct-4-ulo-4,8-pyranosononitrile (3) and 2-deoxy-4,5:6,8-di-O-isopropylidene-α-L-gulo-oct-4-ulo-4,7-furanosononitrile (5) were prepared by a high stereocontrolled indium-mediated Reformatsky-type reaction of 2,3:4,5-di-O-isopropylidene-β-D-arabino-hexos-2-ulopyranose (1) and 2,3:4,6-di-O-isopropylidene-α-L-xylo-hexos-2-ulofuranose (2) with bromoacetonitrile, repectively. The configurations at C(3) in 3 and 5 were established by chemical correlation.