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.
","abstract_html":"<p>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).</p><p>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.</p><p> 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.</p>","abstract_has_math":false,"creators":["Miyai, Kenji"],"institution":null,"degree_name":"Master of Science (M.S.)","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Howard K. Zimmerman, Jr."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1965,"date_issued":"1965-01-01T08:00:00Z","date_published":"1965-01-01T08:00:00Z","updated_at":"2026-07-24T05:37:34Z","subjects":["Glucosides","Amino sugars","Chemistry"],"languages":[],"rights":[],"rights_urls":["http://rightsstatements.org/vocab/NKC/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://scholarlycommons.pacific.edu/uop_etds/1601","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Howard K. Zimmerman, Jr."]},{"key":"dc:creator","label":"Author","values":["Miyai, Kenji"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2018-06-29T08:42:05Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science (M.S.)"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Glucosides","Amino sugars","Chemistry"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:rights","label":"Dc Rights","values":["http://rightsstatements.org/vocab/NKC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://scholarlycommons.pacific.edu/uop_etds/1601"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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.
"]},{"key":"dc:source","label":"Dc Source","values":["36"]},{"key":"dc:title","label":"Title","values":["Derivatives of benzyl n-benzoyl-a-d-glucosaminide"]}]}],"canonical_facts":{"dc:contributor":["Howard K. Zimmerman, Jr."],"dc:creator":["Miyai, Kenji"],"dc:date.available":["2018-06-29T08:42:05Z"],"dc:description.abstract":["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.
"],"dc:identifier":["https://scholarlycommons.pacific.edu/uop_etds/1601"],"dc:rights":["http://rightsstatements.org/vocab/NKC/1.0/"],"dc:source":["36"],"dc:subject":["Glucosides","Amino sugars","Chemistry"],"dc:title":["Derivatives of benzyl n-benzoyl-a-d-glucosaminide"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science (M.S.)"]},"updated_at":"2026-07-24T05:37:34Z"}