Glucosylamine 2,3,4,6-tetraacetate

An interesting variety of compound of this type has been obtained by treating A -methylsulfonyl-D-glucosylamine tetraacetate with methanolic ammonia. The compounds are shown in acyclic form. 

Deacetylatioii of the esters, which proceeds normally, has been siu cess-fully carried out with ammonia, sodium methoxide, or barium methoxide in methanol. In this way, for example, iV-p-tolyl-/8-D-glucosylamine 2,3,4,()-tetraacetate is converted into iV -p-tolyl-/8-D-gluoosylamine, and iV-acetyl-/8-D-galactosylamine tetraacetate into iV-acetyl-/8-D-galactosyl-amine. ... 

Niemann and Hays later showed that the oxidation of one mole of iV-acetyl-D-glucosylamine by lead tetraacetate involves the slow consumption of slightly more than two moles of oxidant, so confirming the result of periodate oxidation. Hockett and Chandler prepared an isomeric N-acetyl-D-glucosylamine, also cyclic since it gives a tetraacetate, by the action of 29 % aqueous ammonia on aldehydo-D-glucose pentaacetate or on hexa-0-acetyl- a -D-glucoheptonic nitrile. The oxidation of this isomer produced formaldehyde (isolated as its 2,4-dinitrophenylhydrazone), but... 

Glucosone, 3-deoxy-o-, 75 Glucosylamine, D-, 225 Glucosyl isocyanate, D-, tetraacetate, 220 Glucosyl isothiocyanate, D-, tetraacetate, 220... 

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