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Synthesis of gem-diamino derivatives on solid support

✍ Scribed by Sonia Cantel; Damien Boeglin; Marc Rolland; Jean Martinez; Jean-Alain Fehrentz

Book ID
104253654
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
89 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Anchoring of an a-amino-acid amide residue by its amine function to a carbamate resin followed by primary amide Hofmann rearrangement led to a gem-diamino residue linked to the resin. The generated primary amine could be acylated with various carboxylic compounds offering a large variety of molecules. Furthermore, this new solid-phase strategy allowed a reliable synthesis of a gem-diamino monomeric residue which could not be easily obtained in solution due to the limited stability of monocarbamate-protected gem-diaminoalkyl derivatives.

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In order to investigate the selective antiproliferative effects shown by 2-(6-hydroxynaphthyl)-b-D-xylopyranoside, the 14 possible b-D-xylopyranosidic compounds were synthesized on solid support. An aminomethylated polystyrene resin was converted into an acid chloride resin and then esterified using