Syntheses of Some Derivatives of D-Glucuronic Acid

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The syntheses of some derivatives of D-glucuronic acid from D-glucofuranurono-6→3-lactone have been investigated. That is, 5-bromo-5-deoxy-1,2-O-isopropylidene-β-L-idofuranurono-6→3-lactone (2) and 5-bromo-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranurono-6→3-lactone (3) were prepared by heating 1,2-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-glucofuranurono-6→3-lactone (1) with lithium bromide in dimethylformamide (DMF); methyl 5-O-(p-toluenesulfonyl)-β-D-glucofuranurono-6→3-lactone, 5-bromo-5-deoxy-α-L-idofuranurono-6→3-lactone, and 5-bromo-5-deoxy-β-D-glucofuranurono-6→3-lactone were prepared by heating 1, 2, and 3 respectively in methanol in the presence of strong acidic ion-exchange resins; 5-deoxy-1,2-O-isopropylidene-α-D-glucofuranurono-6→3-lactone (7) was prepared by the reaction of 2 with thiolacetic acid of benzylmercaptan in pyridine or by the reaction of 2 with triethyl phosphite; 5-bromo-5-deoxy-1,2-O-isopropylidene-β-L-ido-hexodialdo-3,6-furanoid(6S)-1,4-furanose (8) was prepared by the reduction of 2 with lithium aluminum hydride; 1,2-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-gluco-hexodialdo-3,6-furanoid-1,4-furanose and 1,2-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-glucofuranose (10) were prepared by the reduction of 1 with lithium aluminum hydride, and 1,2;3,6-di-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-glucofuranose and 3,6-di-O-acetyl-1,2-O-isopropylidene-5-O-(p-toluenesulfonyl)-α-D-glucofuranose were prepared by the acetonation and the acetylation of 10 respectively.
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Syntheses of Some Derivatives of D-Glucuronic Acid

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