Campus Access Only

All rights reserved. This publication is intended for use solely by faculty, students, and staff of University of the Pacific. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means, now known or later developed, including but not limited to photocopying, recording, or other electronic or mechanical methods, without the prior written permission of the author or the publisher.

Date of Award

1965

Document Type

Thesis

Degree Name

Master of Science (M.S.)

Department

Chemistry

First Advisor

Howard K. Zimmerman, Jr.

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.

Pages

36

Included in

Chemistry Commons

Share

COinS
 

Rights Statement

Rights Statement

No Known Copyright. URI: http://rightsstatements.org/vocab/NKC/1.0/
The organization that has made the Item available reasonably believes that the Item is not restricted by copyright or related rights, but a conclusive determination could not be made. Please refer to the organization that has made the Item available for more information. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use.