Abstract
Brief treatment of 2-acetamido-2-deoxy- D-gluconic acid ( 3) with boiling acetic acid affords, after purification, 2-acetamido-2-deoxy- D-glucono-1,4-lactone ( 1). The same lactone may also be prepared through hydrolytic cleavage of the isopropylidene group in 2-acetamido-2-deoxy-5,6- O-isopropylidene- D-glucono-1,4-lactone ( 4). When the mixture of compounds obtained by the oxidation of 2-acetamido-2-deoxy- D-glucose was treated with an isopropylidenating agent, the crystalline lactone 4 was among the products isolated. In addition, in the course of that reaction, isopropylidene acetals of 2-acetamido-2-deoxy- D-gluconic acid esters, 6– 8 and 9, were formed. When 4 was treated with p-toluenesulfonyl chloride in pyridine, β-elimination occurred to yield 2-acetamido-2,3-dideoxy-5,6- O-isopropylidene- D- erythro-hex-2-enono-1,4-lactone ( 10). With methanol, 4 gave methyl 2-acetamido-2-deoxy-5,6- O-isopropylidene- D-gluconate ( 7), which spontaneously reverted to 4. The susceptibility of lactone derivatives to the action of alcohols is briefly discussed.
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