The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
Copyright policy )The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
Abstract 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.
- Artois University France
- Normandie Université France
- University of Picardie Jules Verne France
[CHIM]Chemical Sciences, 540
[CHIM]Chemical Sciences, 540
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