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Date of Award
Master of Science (M.S.)
Howard K. Zimmerman, Jr.
Within the past few decades, interest in the field of aminosugar chemistry has been stimulated to a remarkable degree and the discovery and syntheses of a wide range of new aminosugars of differing types, for example of two monoamino-tetroses (12,19), nineteen monoamino-pentoses, two diamino-pentoses, thirty-three monoamino-hexoses, and eighteen diamino-hexoses (20) have been accomplished. It is well undterstood that the aminosugars, significant constituents in mnay biologically important materials (11), consist of substances that may be regarded a teh condesation products of an amine and a carbohydrate. Falling into this category are the 2-amino-hexoses which may be derived conceptually as the condensation of ammonia with carbon atom number 2 or a hexose. (4). Thus, D-glucose is the conceptual parent of D-glucosamine (i.e., 2-amino-2-deoxy-D-Glucose).
D-allosamine is one of the rarer aminosugars about which very little is know concerning chemical properties and derivatives. A few studies have recently been made on the beta series of benzyl D-allosaminides after it was shown by Gross et al. (5) that the use of benzyl N-benzoyl-4, 6-0-benzylidene-β-D-glucosaminide as an intermediate in the synthesis of D-allosamine derivative proved fruitful for large-scale preparation of the β-D-allosaminide derivatives. This basic work has established conditions which have made it possible and desireable to conduct also an investigatin into the chemistry of the alpha series of D-allosaminides. Thus it appeared that a procedure involving the benzyl N-benzoyl-α-D-glucosaminide might well afford the alpha anomeric D-allosaminides.
Although several benzyl N-benzoyl-hexosaminides are known (1,5,20), no information is yet available in the literature about benzyl N-benzoyl-α-D-glucosaminide from the standpoint of chemical properties and derivatives. To explore processes from making derivatives of D-allosamine particularly in the series of alpha-anomers, it is necessary to investigate the chemistry of benzyl N-benzoyl-α-D-glucosaminide and its derivatives, preparatory to an attempt to enter the alphaseries of D-allosaminides. Therefore, the principal interest of this investigation was to prepare and to investigate properties of benzyl N-benzoyl-α-D-glucosaminide and its derivatives, and to explore its utility as a possible precursor for the preparation of benzyl 3-0-benzoyl-α-D-allosaminide hydrochloride by the method analogous to the synthesis of the corresponding beta-anomer.
Miyai, Kenji. (1965). Derivatives of benzyl n-benzoyl-a-d-glucosaminide. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/1601