Preparation of 2-amino-2-deoxy-3,4,5,6-tetra- O-methyl- d-gluconic acid hydrochloride, an intermediate in the preparation of polypeptide-type polyamides

Carbohydrate based polyamides are of interest as biomaterials. The authors reported before the synthesis of some derivatives of 6-amino-6-deoxy-D-gluconic acid that are precursors for the synthesis of linear polyamides. Attempts to use 2-amino-2-deoxy-D-gluconic acid and its 4,6-O-benzylidene deriva...

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Bibliographic Details
Published in:Carbohydrate research 1993-01, Vol.240, p.301-305
Main Authors: de Gracia, María, Martin, García, de Paz Báñez, María Violante, Galbis Pérez, Juan A.
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:Carbohydrate based polyamides are of interest as biomaterials. The authors reported before the synthesis of some derivatives of 6-amino-6-deoxy-D-gluconic acid that are precursors for the synthesis of linear polyamides. Attempts to use 2-amino-2-deoxy-D-gluconic acid and its 4,6-O-benzylidene derivative in the synthesis of polypeptides were not successful due to the interference by the hydroxyl groups. In this note they report the preparation of 2-amino-2-deoxy-3,4,5,6-tetra-O-methyl-D-gluconic acid hydrochloride and its transformation into 4-(D-arabino-tetrametoxybutyl)-1,3-oxazolidine-2,5-dione, which is an active monomer for polymerization reactions.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(93)84193-A