Process for preparing 2-deroxy-3-desamino-2,3-epimino-aminoglycosides and intermediates useful therein

Claim 1

IN THE PROCESS FOR PREPARING A 2'''' DEOXY-3'''' -DESAMINO2'''',3'''' -EPIMINO-4,6-DI-(AMINOGLYCOSYL)-2-DEOXYSTREPTAMMINE WHEREIN AN ANTIBACTERIALLY ACTIVE 4,6-DI (AMINOGLYCOSYL) -25DEOXYSTREPTAMINE HAVING A 2'''' -HYDROXY FUNCTION AND A 3''''PRIMARY OR SECONDARY AMINO FUNCTION, THE PRIMARY AND SECONDARY AMINO GROUPS OF WHICH ARE PROCTED BY CARBOBENZYLOXY GROUPS AND PRIMARY AND SECONDARY HYDROXYL GROUPS OF WHICH ARE CONVERTED TO A TRIPHENYLMETHYL ETHER OFA PRIMARY HYDROXYL GROUP OR ACYCLIC KETAL OR ACETAL OF PROTECTABLE NEIGHBORING HYDROXYL GROUPS, IS TREATED WITH A HYDROCARBONSULFONYL HALIDE IN ATERIARY AMINE, THE THEREBY FORMED 2'''' -OHYDROCARBONSULFONY-2-N-CARBOBENZYLOXY 4,6-DI-( (AMINOGLYCOSYL)-2-DEOXYSTREPTAMINE IS TREATED WITH HYDROGEN IN THE PRESENCE OF A CATALYST, OR WITH AN ALKALI METAL IN LIQUID AMMONIA, WHEREBY THE N-CARBBOBENZYLOZY GROUPS ARE REMOVED; AND THE RESULTING 2'''' -O-HYDROCARBONSULFONYL 4,6-DI-( AMINOGLYCOSYL)-2-DEOXYSTREPTAMINE IS CONVERTED TO A 2''''DEOXY-3''''-DESAMINO-2'''',3''''-EPIMINO 4,6-DI(AMINOGLYCOSYL)2-DEOXYSTREPTAMINE BY SPONTANEOUS TRANSFORMATION OR BY HEATING IN A LOWER ALKANOL ALONE OR TOGETHER WITH AN ALKALI METAL SALT OF SAID ALKANOL; THE IMPROVEMENT WHICH COMPRISES PROTECTING PRIMARY AMINO GROUPS AND SECONDARY AMINO GROUPS CAPABLE OF OXAZOLIDINE FORMATION WITH AN ALDEHYDE AND A NEIGHBORING HYDROXYL GROUP M SAID ANTIBACTERIAL ACTIVE 4,6-DI(AMINOGLYCOSYL)-2-DEOXYSTREPTAMINE BY SCHIFF BASEOXAZOLIDINE CONDENSATION PRODUCTS WITH AN ALDEHYDE DEVOID OF HYDROXYL GROUPS; AND, AFTER PREPARATION OF THE 2''''-O-HYDROCARBONSULFONYL ESTER THEREOF, TREATING THE RESULTING 2''''-O-HYDROCARBONSULFONYL 4,6-DI(AMINOGLYCOSYL)-2- DEOXYSTREPTAMINE HAVING NPROCTECTING-SCHIFF BASE -OXAZOLIDINE GROUPS WITH DILUTE AQUEOUS ACID TO A PH IN THE RANGE OF FROM ABOUT 1 TO ABOUT 5, WHEREBY SAID N-PROTECTING SCHIFF BASEOXAZOLIDINE GROUPS ARE REMOVED.