Process for the preparation of 5-fluoro-5-deoxy and 5-epi-fluoro-5-deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols and novel 5-fluoro-5-deoxy and 5-epi-fluoro-5-deoxy derivatives produced thereby

The process of preparing 5-fluoro-5-deoxy or 5-epi-fluoro-5-deoxy derivatives of 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols or their l-N-X derivatives, wherein X is 13 CH.sub.2 Y or ##STR5## wherein Y is a member selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, aminoalkyl, alkylaminoalkyl, aminohydroxyalkyl and alkylaminohyroxyalkyl, said Y having up to 4 carbon atoms and when substituted by both amino and hydroxy groups, said groups are on different carbon atoms;

• which comprises the reaction of dialkylaminosulfur trifluoride with a 4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol or its l-N-X derivative, having all of its amino and hydroxyl functions other than the 5-epi-hydroxyl or 5-hydroxyl function protected, in an inert organic solvent in the temperature range of from about -100.degree. C. to about -50.degree. C., followed by removal of the amino and hydroxyl protecting groups from the so-produced 5-fluoro-5-deoxy or 5-epi-fluoro-5-deoxy-N-protected-O-protected-4,6-di-O-(aminoglycosyl)-1,3- diaminocyclitol, or its l-N-X derivative.