SYNTHESIS OF O-[2-ACETAMIDO-2-DEOXY-6-O-STEAROYL- AND LNORMURAMOYL-L-ALPHA-AMINOBUTANOYL-D-ISOGLUTAMINE, LIPOPHILIC DISACCHARIDE ANALOGS OFMDP

Silver triflate-promoted condensation of acetyl-2-deoxy-2-phthalimido- beta-D-glycopyranosyl bromide (1) with benzyl -O-(methoxycarbonyl)meth yl-alpha-D-glycopyranoside (4) afforded the key compound, benzyl D-glu copyranosyl)-alpha-D-glucopyranoside(5),which after deprotection was t ransformed into acid 10. Condensation of 10 with the benzyl ester of L -alpha-aminobutanoyl-D-isoglutamine and deisopropylidenation of the pr oduct 11 afforded the benzyl eater of N-{2-O[benzyl eta-D-glycopyranos yl)-6-O-benzyl-2,3-dideoxy-alpha -D-glucopyranosid-3-yl]glycoloyl}-L-a lpha- aminobutanoyl-D-isoglutamine (12). Partial O-acylation of 12 and hydrogenolysis of protecting groups gave the 6-O-stearoyl- and (2-tet radecylhexadecanoyl)-disaccharide-dipeptides 17 and 18, respectively. Pyrogenicity and adjuvant activity in cell-mediated immunity are repor ted.