The Synthesis Of 1, 2-O-isopropylidene-α-D-pentadialdo-1, 4-furanose And Oxime Derivatives

1,2-O-isopropylidene-α-D-pentadialdo-1,4-furanose and its oxime derivatives are versatile precursor of bioactive natural products and azasugar and modified sugars. In this paper, five of the derivatives were synthesized.1,2:5,6-di-O-isopropylidene-α-D-glucofuranose was synthesized from D-glucose with the yield of 80%. The stereo-configuration of C-3 was inverted by the CrO3 oxidation/NaBH4 reduction continuous method and the yield was 61.3%. The treatment procedure of oxidation was simplized and the reaction time needed was shortened.3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose and -glucofuranose were synthesized and the hydrolysis of 3-O-benzoyl-1,2:5,6-di-O-isopropylidene- -α-D-allofuranose were studied. The continuous method of benzoylation and hydrolysis was demonstrated. 3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose and -glucofuranose were synthesized with the yield of 66.5% and 57.3% . The selectively hydrolysis of 1,2:5,6-di-O-isopropylidene-α-D-allofuranose and -glucofuranose were also studied in this paper.The vicinal glycol cleavage oxidation of 3-O-benzoyl-1,2-O-isopropylidene-α-D- -allofuranose and -glucofuranose using silica gel-supported NaIO4 was achieved. 3-O-benzoyl-1,2-O-isopropylidene-α-D-ribopentadialdo-1,4-furanose and 3-O- -benzoyl-1,2-O-isopropylidene-α-D-xylopentadialdo-1,4-furanose were obtained with the yield of 81.0% and 65.0%. The structures of the aldehyde compounds were confirmed by 1H-NMR. This method is efficient and facile, and the products obtained are pure enough for further synthetic operations without the need for chromatography.3-O-benzoyl-1,2-O-isopropylidene-α-D-ribopentadialdo-1,4-furanose oxime and O-methyl oxime and 3-O-benzoyl-1,2-O-isopropylidene-α-D-xylopentadialdo-1,4- furanose O-methyl oxime were synthesized, and their structures were confirmed by ~1H-NMR.