Abstract
Acetonation of D-allose in the presence of sulfuric acid gives 2,3:5,6-di- O-isopropylidene-β- D-allofuranose ( 4) in good yield. Oxidation of 4 with methyl sulfoxide and acetic anhydride gave 2,3:5,6-di- O-isopropylidene- D-allono-1,4-lactone (7). Compound 4 was also obtained from 1,2:5,6-di- Oisopropylidene-α- D-allofuranose ( 1) in one step by an acetal-migration reaction. The acetonation of D- ribo-hexulose ( D-psicose) in the presence of anhydrous copper sulfate and sulfuric acid has been re-examined, and the main product has been shown to be 1,2:3,4-di- O-isopropylidene- D-psicofuranose ( 12), by conversion of 12 into 6-deoxy- D-psicose ( 16) through 1,2:3,4-di- Oisopropylidene-6- O-p-tolylsulfonyl- D-psicofuranose ( 14).
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