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

<p>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).</p><p>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.</p><p>The object of this project is to synthesize methyl N-acetyl &alpha;-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 &alpha;-D-idospyradoside by ammonolysis of methyl 2,3-anhydro 4,6-benzylidene &alpha;-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.</p><p>In short, the above route involved essentially a direct conversion from the idose series into the talose series which is illustrated in Scheme I.</p>

Name thesis:degree_name

Master of Science (M.S.)

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

1967

Author dc:creator

• Choudhary, Mohammad Saleem

Contributors dc:contributor

• Paul H. Gross

• Amino sugars
• Glucosides Synthesis
• Chemistry
• Physical Sciences and Mathematics

Licence

• http://rightsstatements.org/vocab/NKC/1.0/

Repository record dc:identifier

https://scholarlycommons.pacific.edu/uop_etds/1638

OAI identifier oai:identifier

oai:scholarlycommons.pacific.edu:uop_etds-2637