Amino peracetylation

Sharpless reaction of the enantiomeric alkenes (47) produced the precursors for 2-amino-2-deoxy-o -D and -L-carba-glucopyranoses. These compounds were converted into the penta-7V,0-acetates by the following sequence. Replacement of the bromo group with an acetate ion, treatment with sodium in liquid ammonia, and peracetylation. 

N. catarrhalis,560 N. perflava,559 Moraxella duplex and Micrococcus calco-aceticus,443 and Escherichia coli,420 Vicari and Kabat,45 in studies of blood-group oligosaccharides, and Hellerqvist and colleagues,53 in an examination of the common core-polysaccharide of Salmonella typhimurium, have used similar methods. The examination of amino sugars as their peracetylated aminodeoxyalditols has also been used by Liideritz and colleagues72 to establish the occurrence of 4-amino-4-deoxy-L-arabinose in Salmonella lipopolysaccharides, and has been extended to aminodeoxyheptoses by Williams and Perry.561... 

Griggs and coworkers343 showed that the decomposition554 of the peracetates of aminodeoxyalditols is minimized if the temperature of the injection port is held below 220°. Furthermore, they identified the product formed from peracetylated 2-amino-2-deoxy-D-glucitol... 

First the amino functionality is protected and the carbohydrate is peracetylated. 

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