Epiglucosamine and Other Altrose Derivatives

In opening the ethylene oxide ring of the methyl anhydroalloside 

Fischer, Bergmann and Schotte had reported that methyl epiglucosamine w as hydrolyzed by acids to a reducing sugar only with great difficulty. Levene and Meyer found that hydrolysis occurred readily enough, but the free sugar was transformed rapidly to a non- 

Throughout this review the shorter terms 3-amino-, 2-chIoro-, etc. have been u.sed instead of 3-desoxy-3-amino-, 2-desoxy-2-chloro-, etc. to indicate tlie replacement of a hydroxyl group by the atom or group named. 

It is of interest to note that the second product to be expected from the addition of ammonia to the anhydromannoside (XLVI), by opening the ethylene oxide ring at carbon atom 2, would be methyl 2-amino-/3-D-glucoside (XLIX). In order to decide whether chitosamine (glucosamine) has a 2-arainoglucose or 2-aminomannose configuration, Haworth, 

Myers and Robertson, and Robertson, Myers and Tetlow, have reported a synthesis of methyl epiglucosamine starting with methyl 2,3-anhydro-4,6-benzylidene-a-D-mannoside (XLIII). By opening the ethylene oxide ring with ammonia they obtained a crystalline product, of m. p. 188° and - -88.9° in chloroform, which was a mixture of 

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