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Title

The synthesis of methyl-2-acetamido-3,4,6-0-triacetyl alpha-D-talosaminide

Author

Mohammad Saleem Choudhary, University of the Pacific

Date of Award

1967

Document Type

Thesis

Degree Name

Master of Science (M.S.)

Department

Chemistry

First Advisor

Paul H. Gross

First Committee Member

Herschel Frye

Second Committee Member

Emerson G. Cobb

Abstract

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.

Pages

32

Recommended Citation

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