Syntheses of naturally occurring fatty acid esters of sucrose and heptose-containing oligosaccharides found in the Salmonella Ra core

Abstract: Nine sucrose esters, acylated in the glucopyranosyl moiety, have been synthesized from the same precursor, 3-0-allyl-3',4',6'-tri-0-benzyl-4,6-0- (4-metoxybenzylidene)sucrose. The sucrose esters synthesized include the major compounds found in tobacco and potato plants, i. e., 6-0-acetyl-2,3,4- tri-0-[3-(S)-methylpentanoyl]sucrose and 2,3-di-0-isobutyryl-6-0- decanoylsucrose.Synthesis of the trisaccharide 2-(4-trifluoracetamidophenyl)ethyl 0-(Lglycero- a-D-manno-heptopyTanosyl)-(l->7)-0-(L-glycero-a-D-mannoheptopyranosyl)-( l -»3)-L-g/ycero-a-D-/nanno-heptopyranoside is described. While still protected, this oligosaccharide is suitable for further reactions. Using this strategy, a tetra-, a penta- and a hexasaccharide, all containing the same triheptoside, were synthesized. All oligosaccharides correspond to stmctures found in the Salmonella Ra core.