Immunologically active dipeptidyl 5-0,6-0-acyl-2-amino-2-deoxy-D-glucofuranose derivatives and methods of preparation

Claim 1

Dipeptidyl 5-O, 6-O-acyl-2-amino-2-deoxy-D-glucofuranoses of the general structural formula: ##STR14## wherein R 1 is C 1-7 alkyl, substituted C 1-7 alkyl; phenyl; or substituted phenyl; wherein the substituent is one or more alkyl groups of 1-3 carbon atoms or hydroxy or mercapto groups either free, or esterified by an alkyl group of 1-3 carbons or esterified by an acid of 1-4 carbons, lower (1-4 C ) alkyldioxy cycloalkyldioxy of 5-7 carbon atoms, amino, trifluoromethyl, halo, or phenyl; R 2 is hydrogen; or C 1-10 alkyl; R 3 and R 4 may be the same or different and are each independently acyl of the formula: ##STR15## where X is --O--, --S--, or ##STR16## R 9 , R 10 , and R 12 may be the same or different and are each independently hydrogen; C 1-20 alkyl; C 1-20 alkylcarbonyloxy; amino; benzyl; C 1-20 alkoxymethyl; or C 1-20 alkylamido; r is 0 or 1; s is 0 or 1; and t is 0-20, provided that s may only be 0 when r and t are greater than 0, or when r is 0 and R 11 is amino, phenyl, substituted phenyl, 1-adamantyl, or heterocycle selected from the group consisting of 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-pyrrolidinyl, 2-, 3-, or 4-pyridyl, and 1-tetrazolyl, said heterocycle optionally substituted with C 1-20 alkylcarbonyl; and R 11 is hydrogen; C 1-30 alkyl; C 2-30 alkenyl; C 1-30 alkoxy; phenyl; C 1-20 alkylsulfonyl; or cholesteryl; and R 4 may additionally be hydrogen; R 5 is hydrogen; or R 5 -R 6 together is --CH 2 --CH 2 --CH 2 ; R 6 is hydrogen; C 1-7 alkyl; hydroxymethyl; mercaptomethyl; benzyl; or substituted benzyl; R 7 and R 8 may be the same or different and are each independently COOR or CONR'R", where R is hydrogen or C 1-7 alkyl, and R' and R" are each independently hydrogen or C 1-3 alkyl; when R 2 is C 1-10 alkyl, the stereochemistry at asymmetric center I can be either D or L; when R 6 is not hydrogen, the stereochemistry at asymmetric center II is L; the stereochemistry at asymmetric center III is D.