173987-64-9

Upstream product

• 115166-92-2 2-[4-(trifluoroacetylamino)phenyl]ethanol 
• 85382-90-7 methyl-4,5,7,8-tetra-O-acetyl-2,6-anhydro-2,3-dideoxy-D-manno-oct-2-enosonat 
• 173987-63-8 (2S,3S,4S,5S,6R)-4,5-Diacetoxy-6-((R)-1,2-diacetoxy-ethyl)-3-phenylselanyl-2-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 173987-68-3 methyl <2-(4-trifluoroacetamidophenyl)ethyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-5-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-α-D-manno-oct-2-ulopyranosid>onate 
• 173987-69-4 methyl <2-(4-trifluoroacetamidophenyl)ethyl 4-O-benzyl-5-O-(2-O-benzyl-α-D-glucopyranosyl)-3-deoxy-7,8-O-isopropylidene-α-D-manno-oct-2-ulopyranosid>onate 
• 173987-67-2 methyl <2-(4-trifluoroacetamidophenyl)ethyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-oct-2-ulopyranosid>onate 
• 173987-66-1 methyl <2-(4-trifluoroacetamidophenyl)ethyl 3-deoxy-7,8-O-isopropylidene-α-D-manno-oct-2-ulopyranosid>onate 
• 173987-65-0 (2R,4R,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-2-{2-[4-(2,2,2-trifluoro-acetylamino)-phenyl]-ethoxy}-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Evaluation of thioglycosides of Kdo as glycosyl donors

The use of Kdo thioglycosides as glycosyl donors using DMTST, IBr/AgOTf and NIS/AgOTf as promoters has been evaluated. Activation at low temperature allowed to escape the formation of 2,3-glycal byproducts to give glycosides in high yield and with good β-

Synthesis of 2-(4-aminophenyl)ethyl 3-deoxy-5-O-(3,4,6-tri-O-β-D-glucopyranosyl-α-D-glucopyranosyl)-α-D-manno-oct-2-ulopyranosidonic acid, a highly branched pentasaccharide corresponding to structures found in lipopolysaccharides from Moraxella catarrhalis

Syntheses of the pentasaccharide 2-(4-aminophenyl)ethyl 3-deoxy-5-O-(3,4,6-tri-O-β-D-glucopyranosyl-α-D-glucopyranosyl)-α-D-manno-oct-2-ulopyranosidonic acid and of the tetrasaccharide 3,4,6-tri-O-β-D-glucopyranosyl-α-D-glucopyranoside, both as its methyl and 2-(4-trifluoroacetamidophenyl)ethyl glycoside, are described.These oligosaccharides correspond to structures found in the lipopolysaccharide of Moraxella catarrhalis and were needed for biological experiments aimed at producing antibodies against the bacteria.The best way to introduce the glucopyranosyl groups into the 3-, 4-, and 6-positions of the branched target compounds was found to be a one-step reaction using a 3,4,6-triol as acceptor and 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl bromide as donor in a silver trifluoromethanesulfonate-promoted coupling.The spacer arm, necessary for the formation of immunoactive glycoconjugates, was introduced into the glucose moiety via a dimethyl(methylthio)sulfonium trifluoromethanesulfonate-promoted reaction using the ethyl thioglucoside as donor, whereas for Kdo, the acetylated glycal derivative, methyl 4,5,7,8-tetra-O-acetyl-2,6-anhydro-3-deoxy-D-manno-oct-2-enonate, was used as donor and phenylselenyl trifluoromethanesulfonate as a stereocontrolling promoter.Keywords: Carbohydrates; Oligosaccharide synthesis; Bacterial antigens; Kdo; Glycoconjugates