2-Aminosugar derivatives of macrolides

A process for preparing a compound of the formula ##STR16## wherein n is 1 or 2;

• R.sup.2 is --OR.sup.0 ;
• R.sup.3 is (C.sub.1 to C.sub.4)alkyl or allyl;
• R.sup.1 and R.sup.0 are each H or ##STR17## R.sup.4 is, for each occurrence, independently --CO.sub.2 R.sup.9, --CO.sub.2 H, H, --CH.sub.3, --CONH.sub.2, --CONHR.sup.9, --CONR.sub.2.sup.9, --CH.sub.2 OCOR.sup.9, --CH.sub.2 OCO.sub.2 R.sup.9, --CH.sub.2 OCONHR.sup.9, --CH.sub.2 OCONR.sub.2.sup.9 or --CH.sub.2 OR.sup.9 ;
• R.sup.5 and R.sup.6 are, for each occurrence, independently (C.sub.1 to C.sub.4)alkoxy benzyloxy, --OCOR.sup.9, --OCO.sub.2 R.sup.9 or --OSiR.sub.3.sup.10 ;
• R.sup.7 and R.sup.8 are, for each occurrence, independently H, (C.sub.1 to C.sub.4)alkyl, --COCH.sub.2 R.sup.9, --COR.sup.9, --CO.sub.2 R.sup.9 or --SO.sub.2 R.sup.9 ;
• R.sup.9 is, for each occurrence, independently (C.sub.1 to C.sub.6)alkyl, (C.sub.3 to C.sub.6) cycloalkyl, allyl, --CF.sub.3, pyridyl, thienyl, thienylmethylene, furanyl, benzyl, benzyl variously substituted with one to five halogen atoms, --OH groups or (C.sub.1 to C.sub.4)alkoxy groups, phenyl or phenyl variously substituted with one to five halogen atoms, --OH groups or (C.sub.1 to C.sub.4)alkoxy groups;
• and
• R.sup.10 is, for each occurrence, independently (C.sub.1 to C.sub.4)alkyl, phenyl or benzyl;
• provided that at least one of R.sup.1 and R.sup.0 is ##STR18## comprising reacting a compound of the formula ##STR19## wherein R.sup.3 is (C.sub.1 -C.sub.3)alkyl and n is 1 or 2 with 2 to 4 molar equivalents of a compound of the formula ##STR20## wherein X is halo;
• R.sup.4 is, for each occurrence, independently --CO.sub.2 R.sup.9, --CO.sub.2 H, H, --CH.sub.3, --CONH.sub.2, --CONHR.sup.9, --CON.sub.2.sup.9, --CH.sub.2 OCOR.sup.9, --CH.sub.2 OCO.sub.2 R.sup.9, --CH.sub.2 OCONHR.sup.9, --CH.sub.2 OCONR.sub.2.sup.9 or --CH.sub.2 OR.sup.9 ;
• R.sup.5 and R.sup.6 are, for each occurrence, independently (C.sub.1 to C.sub.4)alkoxy, benzyloxy, --OCOR.sup.9, --OCO.sub.2 R.sup.9 or --OSiR.sub.3.sup.10 ;
• R.sup.7 and R.sup.8 are, for each occurrence, independently H, (C.sub.1 to C.sub.4) alkyl, --COCH.sub.2 R.sup.9, --COR.sup.9, --CO.sub.2 R.sup.9 or --SO.sub.2 R.sup.9 ;
• R.sup.9 is, for each occurrence, independently (C.sub.1 to C.sub.6)alkyl, (C.sub.3 to C.sub.6)cycloalkyl, allyl, --CF.sub.3, pyridyl, thienyl, thienylmethylene, furanyl, benzyl, benzyl variously substituted with one to five halogen atoms, --OH groups or (C.sub.1 to C.sub.4)alkoxy groups, phenyl or phenyl variously substituted with one to five halogen atoms, --OH groups or (C.sub.1 to C.sub.4)alkoxy groups;
• and R.sup.10 is, for each occurrence, independently (C.sub.1 to C.sub.4) alkyl, phenyl or benzyl in the presence of a drying agent selected from the group consisting of molecular sieves, calcium sulfate and magnesium sulfate;
• a base selected from the group consisting of mercuric carbonate, silver carbonate, mercuric nitrate and silver nitrate;
• and a catalyst selected from the group consisting of silver triflate, silver perchlorate, silver tetrafluoroborate, mercuric triflate, mercuric perchlorate and mercuric tetrafluoroborate in a reaction inert solvent at about -78.degree. C. to about -70.degree. C. with warming to about 0.degree. C. for about 0.5 to about 24 hours and subsequent stirring at room temperature for about 0.5 to about 24 hours.