The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
| Autor: | Imane Stasik, Daniel Beaupère, Ludovic Chaveriat, Gilles Demailly |
|---|---|
| Přispěvatelé: | Unité Transformations & Agroressources [Université d'Artois] (UTA), Université d'Artois (UA)-Transformations et Agro-ressources (UT&A), UniLaSalle-UniLaSalle, Laboratoire de Glycochimie, des Antimicrobiens et des Agro-ressources - UMR CNRS 7378 (LG2A ), Institut de Chimie du CNRS (INC)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2006 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Galactitol 010402 general chemistry 01 natural sciences Catalysis Neutralization 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Monomer Nylon 6 chemistry Polymer chemistry medicine [CHIM]Chemical Sciences Organic chemistry Mannitol Physical and Theoretical Chemistry ComputingMilieux_MISCELLANEOUS Catalytic hydrogenation Saponification medicine.drug |
| Zdroj: | Tetrahedron: Asymmetry Tetrahedron: Asymmetry, Elsevier, 2006, 17 (9), pp.1349-1354. ⟨10.1016/j.tetasy.2006.04.018⟩ |
| ISSN: | 0957-4166 |
| Popis: | 6-Azido-6-deoxy- d -galactitol and d -mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6-deoxy- d -hexono-1,4-lactones, and 6-azido-6-deoxy- d -glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95–98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy- d -aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy- d -hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82–88% overall yields. |
| Databáze: | OpenAIRE |
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