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Date of Award

1967

Document Type

Dissertation - Pacific Access Restricted

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Chemistry

First Advisor

WH Wadman

First Committee Member

Carl C. Rudeul

Second Committee Member

Herschel Frye

Third Committee Member

Charles A. Matuszak

Fourth Committee Member

Paul Gross

Abstract

A great variety of amino sugars has been found in antibiotics among these D-gulosamine in the striptomyces group. In the same group, .an N-methylated amino-sugar, N-methyl-L~ glucosamine has been isolated. Although N-methyl-0-gulosamine .has not been found in nature until now, its ultimate discovery would not be surprising in this context. In the present work this amino-sugar and some important derivatives are prepared for the first time, starting from D-glucosamine, a pure benzyl· 3-0-acetyl-2-benzyloxycarbonylamido-2-deoxy-~-D-glucopyranoside (X) was obtained by a series of kno~n processes. Benzyl 3-0-acetyl~-methylsulfonyl-2-deoxy-~-D-glucopyranoside (XIII) and some of its derivatives were obtaine.d from (X). An attempt was made to obtain benzyl-~-D~gulopyranoside (2'3':4,5)oxazolidone- 2 (XVII), by a route different from that of Gross et al. Since the yield of the starting material (XIII) to be use~for the preparation of the oxazolidone (XVII) was not high enough, the oxazolidone (XVII), which was the starting material for this investigation, was synthesized in the original manner.

When positions 4 and 6 of the oxazolidone (XVII) were blocked by the benzylidene group, methylation occurred only at the nitrogen. Mono-N-methyl-gulosamine (XXV) and some of its derivatives were synthesized in this way. when only the 6-posi tion of the oxazolidone (XVII) was blocked, the hydroxyl group in the 4-position was also methylated. In this way, the 4-0-methyl ether of N-methyl-0-gulosamine (XXXI) could be synthesized. The 4,6-0-methyl ether of N-methyl-D-gulosamine (XXXVI) was synthesized by direct methylation of the oxazolidone (XVII) and subsequent cleavage of the blocking groups.

Pages

87

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