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Date of Award
Doctor of Philosophy (Ph.D.)
First Committee Member
Carl C. Rudeul
Second Committee Member
Third Committee Member
Charles A. Matuszak
Fourth Committee Member
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.
Noorzad, Hazrat Mohammed. (1967). Synthesis Of N-Methyl-D-Gulosamine And Methyl Ethers Of N-Methyl-D-Gulosamine. University of the Pacific, Dissertation. https://scholarlycommons.pacific.edu/uop_etds/2829
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