Electron-transfer reduction of 1-deoxy-1-nitroalditols to glycamines with ferrous hydroxide.

Autor: Pribulová B; Institute of Chemistry, Center for Glycomics, GLYCOMED, Slovak Academy of Sciences, SK-84538 Bratislava, Slovakia., Petrušová M, Smrtičová H, Petruš L
Jazyk: angličtina
Zdroj: Carbohydrate research [Carbohydr Res] 2012 Dec 01; Vol. 363, pp. 62-5. Date of Electronic Publication: 2012 Oct 12.
DOI: 10.1016/j.carres.2012.10.004
Abstrakt: Treatment of eight different 1-deoxy-1-nitroalditols with freshly prepared ferrous hydroxide at ambient temperature provides the corresponding glycamines that were isolated in 81-94% yields as salts with TFA. Under such modified reaction conditions, the retro-Henry reaction of the starting compounds is significantly suppressed due to the amphoteric character of the reducing agent in water. Lower, 58-75% yields were obtained by the classical process with ferrous sulfate in aqueous ammonia and employing an improved purification procedure for the product glycamines by irreversible capture of sulfate ions with barium carbonate.
(Copyright © 2012 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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