GB811510A - New nitrogen-containing derivatives of polyhydroxy compounds and process for the preparation thereof - Google Patents

Abstract

The invention comprises mono-, bis- and tri-b -halo-ethylamino-derivatives of hexoses, hexitols and derivatives thereof having substituted hydroxyl groups (e.g. acetals, cyclic acetals, thioacetals and semi-acetals), and a process for their preparation by reacting an ethyleneimino derivative of a hexose, hexitol or a derivative thereof having substituted hydroxyl groups, with a hydrogen halide, and if required removing any hydroxyl group substituents. The intermediate ethylene-imino compounds may be prepared by reacting an epoxide of a hexose, hexitol, or derivative thereof, with ethylene imine and if required removing any hydroxyl group substituents. Specified hexoses and hexitols are glucose, mannose, galactose, mannitol and sorbitol, and particular hydroxyl derivatives include isopropylidene and benzylidene derivatives, mercaptals, mercaptols and glucosides, while suitable epoxide starting materials are 5,6 - anhydro - 1,3 - 2,4 - diethylidene - D-sorbitol, 1,2 - 3,4 - di - isopropylidene - 5,6 - anhydro - D - mannitol, 1 - p - toluenesulpho - 2,4-benzol - 5,6 - anhydro - D - sorbitol, methyl 2,3-anhydro - b - D - mannopyranoside, 4,6-benzylidene - 2,3 - anhydro - a - methylmannoside, and methyl 3,4-anhydro-b -D-galactopyranoside. In examples: (1) 1,6-bis-ethyleneimino - 1,6 - desoxy - 3,4 - isopropylidene - D-mannitol (prepared by the addition of ethyleneimine to 1,2-5,6-di-anhydro-3,4-isopropylidene-D-mannitol) in methanol is added slowly to cooled, concentrated HCl, yielding crystals of 1,6 - bis - (b - chloro - ethylamino) 1,6 - desoxy-D-mannitol dihydrochloride; (2) 1,2-isopropylidene - 6 - ethyleneimino - 6 - desoxy - D - glucofuranose (prepared by addition of ethyleneimine to ethereal 5,6-anhydro-1,2-isopropylidene-D-glucose) similarly yields 6-mono-(b -chloroethylamino) 6-desoxy-D-glucofuranose.