J. Jacquinet, Pierre Sinaÿ
May 1, 1974
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Influential Citations
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Journal
Carbohydrate Research
Abstract
Abstract Methyl 2-acetamido-5,6-di- O -benzyl-2-deoxy-β- d -glucofuranoside (11) was obtained in six steps from the known methyl 3- O -allyl-2-benzamido-2-deoxy-5,6- O -isopropylidene-β- d -glucofuranoside. Mild acid hydrolysis, followed by benzylation gave the 5,6-dibenzyl ether. The benzamido group was exchanged for an acetamido group by strong alkaline hydrolysis, followed by N -acetylation, and the allyl group was isomerized into a 1-propenyl group that was hydrolyzed with mercuric chloride. Treatment of 11 with l -α-chloropropionic acid and with diazomethabe gave methyl 2-acetamido-5,6-di- O -benzyl-2-deoxy-3- O -[ d -1-(methoxycarbonyl)ethyl]-β- d -glucofuranoside which formed on mercaptolysis the internal ester 16 , further converted into 2-acetamido-4- O -acetyl-5,6-di- O -benzyl-2-deoxy-3- O -[ d -1-(methoxycarbonyl)ethyl]- d -glucose diethyl dithioacetal (18) by alkaline treatment followed by esterification with diazomethane and acetylation. Attempts to remove the O -acetyl group of the corresponding dimethyl acetal 20 with sodium methoxide in mild conditions were not successful.