Abstract
The known 3,4,5-tri- O-benzoyl-2-deoxy- d- erythro-pentose (prepared in three steps from 2-deoxy- d- erythro-pentose) was oxidized to 3,4,5-tri- O-benzoyl-2-deoxy- d- erythro-pentonic acid, which was converted into the corresponding acid chloride. Treatment of the acid chloride with ethereal diazomethane afforded the diazomethyl ketone, which underwent reduction to give crystalline 4,5,6-tri- O-benzoyl-1,3-dideoxy- d- erythro-hexulose, obtained alternatively, in 46% yield, by the action of diazomethane on 3,4,5-tri- O-benzoyl-2-deoxy- d- erythro-pentose. Mercaptalation of the benzoylated 1,3-dideoxy- d- erythro-hexulose with methanethiol yielded syrupy 4,5,6-tri- O-benzoyl-1,3-dideoxy- d- erythro-hexulose dimethyl dithioacetal which, on debenzoylation, gave 1,3-dideoxy- d- erythro-hexulose dimethyl dithioacetal (likewise a syrup), which was converted into crystalline 6- O-adamantoyl-1,3-dideoxy- d- erythro-hexulose dimethyl dithioacetal. Debenzoylation of 4,5,6-tri- O-benzoyl-1,3-dideoxy- d- erythro-hexulose afforded 1,3-dideoxy- d- erythro-hexulose as an impure syrup.
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