297733-60-9

Upstream product

• 297733-56-3 N-{4-[2-((2R,4aR,6S,7S,8R,8aS)-7,8-Diazido-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-ethyl]-phenyl}-2,2,2-trifluoro-acetamide 
• 297733-53-0 (1aR,2S,3aR,6R,7aR,7bR)-2-Ethylsulfanyl-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 115166-92-2 2-[4-(trifluoroacetylamino)phenyl]ethanol 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 1043887-04-2 ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-α-D-glucopyranoside 
• 297733-58-5 2-(p-trifluoroacetamidophenyl)ethyl 2,3-diazido-6-O-benzyl-2,3-dideoxy-α-D-mannopyranoside 
• 297733-52-9 ethyl 4,6-O-benzylidene-3-O-p-toluenesulfonyl-1-thio-β-D-glucopyranoside 
• 297733-55-2 ethyl 2,3-diazido-4,6-O-benzylidene-2,3-dideoxy-1-thio-β-D-mannopyranoside 
• 297733-54-1 ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-altropyranoside 

Downstream Products

• 297733-61-0 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-((2S,3S,4R,5S,6S)-4,5-bis-acetylamino-2-formyl-6-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

Synthesis of a spacer-containing disaccharide fragment of Bordetella pertussis lipopolysaccharide

The disaccharide 2-(p-aminophenyl)ethyl 4-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-2,3-diacetamido-2,3-dideoxy-α-D-mannopyranoside uronate, which is assumed to be a partial structure of the Bordetella pertussis polysaccharide, was synthesized starting from D-glucose and D-glucosamine, respectively. The major synthetic transformations were conversion of D-glucosamine into the donor ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside and conversion of glucose, by a sequence involving 2,3-epoxide formation/opening, nucleophilic triflate displacement in the 3-position, and necessary protecting group manipulations, into the acceptor 2-(p-trifluoroacetamidophenyl)ethyl 6-O-benzyl-2,3-diazido-2,3-dideoxy-α-D-mannopyranoside. Coupling of the donor and acceptor units promoted by dimethyl(methylthio)sulfonium triflate followed by selective oxidation of the 6'-position and deprotection gave the target disaccharide. Copyright (C) 2000 Elsevier Science Ltd.