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Cyclic Derivatives Of 2-Amino-2-Deoxy-D-Hexopyranoses

Author

Kenji Miyai, University of the Pacific

Date of Award

1968

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Chemistry

First Advisor

Emerson G Cobb

First Committee Member

Paul Gross

Second Committee Member

C H Roscoe

Third Committee Member

Donald K Wedegaertner

Fourth Committee Member

Howard K Zimmerman

Fifth Committee Member

W H Wadma

Sixth Committee Member

Colin Patts

Abstract

The purpose of this investigation was to prepare heterocyclic derivatives, bridging C-2 and C-3 of 2-amino-2-deoxy-D-hexopyranoses, useful as blocking groups in the preparation of aminosugar oligosaccharides and polysaccharides. The work reported herein is concerned with oxazolidones of 2-amino-2-deoxy-D-hexopyranoses (Figure 1).)

There are no examples known, in which five or six-membered rings are fused in a trans-arrangement to five-membered furanose ring. However, although synthetic difficulties were observed, sic and five-membered rings were fused in a trans-arrangement to a sic-membered pyranose ring as pointed out before. In the case of our trans-diequatorially fused oxazolidones additional preparative difficulties were expected, because of the possibility of opening and recyclization of the less stable trans-oxazolidone to form the more stable cis-oxazolidone (39).

The amino sugars that have the hydroxyl group at C-3 in the cis-position to the amino group, but otherwise the same structure as D-allopyranose and 2-amino-2deoxy-D-gulopyranose, respectively. Thus, it was considered expedient that oxazolidones of D-allosamine and D-glucosamine be investigated prior to the investigation of oxazolidones of D-glucosamine.

Pages

105

Recommended Citation

Miyai, Kenji. (1968). Cyclic Derivatives Of 2-Amino-2-Deoxy-D-Hexopyranoses. University of the Pacific, Dissertation. https://scholarlycommons.pacific.edu/uop_etds/2827