title: Total synthesis of X hapten, III3 Fuc alpha-nLc4 Cer.
abstract: Total synthesis of O-beta-D-galactopyranosyl-(1----4)-O-[alpha-L- fucopyranosyl- (1----3)]-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta- D- galactopyranosyl- (1----4)-O-beta-D-glucopyranosyl-(1----1)-2-N-tetracosanoyl-(2S,3R ,4E)- sphingenine was achieved by use of the key glycosyl donors O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-(1----4)-O-[(2,3,4-tri-O-acetyl-alpha-L-fucopyranosyl) - (1----3)]-O-(2- acetamido-6-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-(2,4,6-tr i-O- acetyl- beta-D-galactopyranosyl)-(1----4)-2,3,6-tri-O-acetyl-alpha-D-glucopyrano syl trichloroacetimidate and fluoride, as well as key glycosyl acceptor 3-O-benzoyl-2-N-tetracosanoyl- (2S,3R,4E)-sphingenine, in an unambiguous manner.
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005732:Gangliosides / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D016256:Lewis X Antigen; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013329:Structure-Activity Relationship
chemical_list: D005732:Gangliosides; D007202:Indicators and Reagents; D016256:Lewis X Antigen