Date of Award
1985
Document Type
Thesis
Degree Name
Master of Science (M.S.)
Department
Graduate School
First Advisor
Paul H. Gross
First Committee Member
Charles A. Matuszak
Second Committee Member
James W. Blankenship
Abstract
The chemistry of amino sugar compounds has been studied in the last years in connection with the study of natural products, and many of them have been isolated. 57,17,18 Amino sugars play an important role in biochemistry, forming blocks of homo- and heteropolymers and complex molecules such as microbial polysaccharides, enzymes, gangliosides, glycoproteins, and antibiotics.
This research project had the purpose of preparing a derivative of 2-amino-2-deoxy-D-glucose, with a free hydroxyl group at the anomeric carbon, with the 4,6-positions blocked with the benzylidene cyclic acetal, and the 2,3-positions being blocked by a 3,3-diphenyl-2-morpholinone ring trans diequatorially fused to the amino sugar ring. The C-1 position was initially protected with a β-benzyl aglycon, which was expected to be removable selectively by catalytic hydrogenation. It was also hoped that we could optimize conditions for the synthesis of the morpholinone derivative. Selective cleavages of the blocking groups were to be investigated.
Pages
58
Recommended Citation
Guardado Puentes, Julian. (1985). Trans diequatorially fused 3',3'-Diphenyl-2'-morpholinone derivatives of 2-Amino-2-deoxy-D-glucose. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/2113
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