New N-Glucosylated Substituted Anilines

Vsevolod Pogrebnoi
2015 Chemistry Journal of Moldova: General, Industrial and Ecological Chemistry  
The reaction of (+)-D-glucose 1 with 4-chloroaniline 6b or 3,5-dibromoaniline 12 leads almost exclusively to the β-confi guration of N-glucosylated anilines 7b and 13. Acetylated derivatives 8b, 14 and 15 were obtained by dissolving/suspending substances 7b and 13 in Ac 2 O/Py mixture. The acetylation of 2-(3,5-dibromophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 13 is less selective than in the case of the 2-(4-chlorophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
more » ... H-pyran-3,4,5-triol 7b and leads to compounds 2-(acetoxymethyl)-6-(3,5-dibromophenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 14 and 2-(acetoxymethyl)-6-(3,5-dibromophenylamino)-5-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate 15 in a 2:1 ratio. The product 14 is formed with greater selectivity and in a higher yield (up to 80%) when the reaction is catalyzed by DMAP and stored for one week at +4 o C.
doi:10.19261/cjm.2015.10(2).08 fatcat:r4hm5btpa5c6vp535pvkin6q54