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Synthesis Of Benzyl Beta D-Gulopyranosiduronic Acid-(2',3': 4,5)-Oxazolidone-2

Author

Gerald Duane Shryock, University of the Pacific

Date of Award

1966

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Chemistry

First Advisor

Emerson G. Cobb

First Committee Member

Donald K. Wedergaertner

Second Committee Member

Richard P. Dodge

Third Committee Member

WH Wadman

Fourth Committee Member

MA Marte

Fifth Committee Member

Howard K. Zimmerman

Abstract

Although D-glucosamine has been found as a constituent of some antibiotics (28), very little research has been carried out in the area of synthetic preparations. Dutcher (7) recently reviewed the biochemical importance of this class of amino sugars as a constituent of complex antibiotic substances which compose the streptothricin family. For a complete elucidation of these antibiotics, it becomes necessary to investigate thoroughly the synthesis and reactions of the D-glucosamine compounds. Gross et al. (12) have succeeded in preparing the oxazolidone of α-D-glucosamine as well as some derivatives (13) of this compound. The present work reports an attempt to prepare the oxazolidone of β-D-glucosamine, its uronic acid, and some uronic acid derivatives. Of special interest is the uronic acid since uronic acids of other compounds have been used as intermediates for several types of reactions. One of the most interesting employments of such intermediates is the use of uronic acids for the indirect introduction of an omega-amino group (27, 29, 30, 33, 34) in syntheses of diamino sugars. Another use of uronic acids is in the so-called transposition reaction, as carried out by Fischer (9) on glucose and later applied to amino sugars by Weidmann et al. (35). This series of reactions involves transposition of the C-1 carbonyl function to C-6 thereby converting 2-amino D-glucose to 5-amino L-gulose. Other uronic acid derivatives may prove useful in the future.

This research problem may be divided into four categories; (i) preparation of a suitable starting material, (ii) an investigation of suitable methods for the preparation of the desired glucosamine compound, (iii) conversion of the glucosamine compound to the uronic acid, and (iv) preparation of the desired uronic acid derivatives.

Pages

51

Recommended Citation

Shryock, Gerald Duane. (1966). Synthesis Of Benzyl Beta D-Gulopyranosiduronic Acid-(2',3': 4,5)-Oxazolidone-2. University of the Pacific, Dissertation. https://scholarlycommons.pacific.edu/uop_etds/2838