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Date of Award
Master of Science (M.S.)
Paul H. Gross
First Committee Member
Second Committee Member
Emerson G. Cobb
Amongst the very many different kinds of amino sugars, theones that have aroused the most interest are the 2-amino 2-deoxy hexoses which are found in such well known antibiotics as streptomycin and neomycine (2). There are so far about forty-three antibiotics which are known to contain different aminosugars (6).
Aminosugars exhibit the same properties as other reducing aldohexoses, e. g. reduction of silver and cupric salts, oxidation to hexonic acids, reduction to alcohols and formation of glycosides.
The object of this project is to synthesize methyl N-acetyl α-D-talosaminide which has previously been prepared by Jeanloz (3) following a different route. The path that jeanloz, Jeanloz, and Glazer (3) followed involved the preparation of methyl 2-acetamide 4, 6-benzylidene 2-deoxy α-D-idospyradoside by ammonolysis of methyl 2,3-anhydro 4,6-benzylidene α-D-idospyranoside which was converted to methyl 2-acetamido 4,6-benzylidene talopyranoaide by treatment with sodium acetate in aqueous 2-methoxyethanol. This compound was debenzylidenated with aqueous acetic acid and acetylated to obtain methyl 2-acetamido 3,4,6-tri-0-acetyl talosaminide.
In short, the above route involved essentially a direct conversion from the idose series into the talose series which is illustrated in Scheme I.
Choudhary, Mohammad Saleem. (1967). The synthesis of methyl-2-acetamido-3,4,6-0-triacetyl alpha-D-talosaminide. University of the Pacific, Thesis. https://scholarlycommons.pacific.edu/uop_etds/1638