138624-50-7

Upstream product

• 29741-69-3 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide 
• 75-08-1 ethanethiol 
• 174172-99-7 ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 
• 5573-62-6 (ethylthio)trimethylsilane 
• 72984-63-5 1,3,4,6-tetra-O-acetyl-2-O-benzyl-α- and β-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 173987-57-0 ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 1372765-77-9 methyl 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 138624-49-4 Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 138624-53-0 Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 138624-52-9 Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((2R,3R,4S,5R,6S)-3,4-diacetoxy-5-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester 
• 138624-51-8 Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-5-benzyloxy-6-ethylsulfanyl-2-trityloxymethyl-tetrahydro-pyran-3-yl ester 
• 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 
• 173987-60-5 2-(4-trifluoroacetamidophenyl)ethyl 2-O-benzyl-α-D-glucopyranoside 
• 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 
• 173987-59-2 2-(4-trifluoroacetamidophenyl)ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 
• 173987-57-0 ethyl 2-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

An expeditious route to the synthesis of adenophostin A

Glycosylation of 1,2-O-isopropylidene-5-O-tert-butyldiphenylsilyl-α-D-ribofuranose (8) with ethyl 3,4,6-tri-O-acetyl-2-O-1-thio-α/β-D-glucopyranoside (7) under the agency of N-iodosuccinimide and trifluoromethanesulfonic acid afforded α-linked dimer 10 in 95% yield. Acetylation of 13, obtained after hydrogenation of 10 followed by pivaloylation of 11 (→12) and deacetonation, yielded penta-acetate 14. Vorbruggen-type condensation of 14 with bis-trimethylsilyl 6-N-benzoyladenine (9) gave adenosyl glucoside 17. Deacetylation of 17 resulted in migration of the pivaloyl group from the 2'-OH to the 3'-OH of the glucosyl moiety (→18), giving access, after phosphorylation and deprotection, to adenophostin A analog 4 containing two (2'-4')-cis oriented phosphate groups. Vorbrugen-type condensation of 9 with 16, obtained by deacetonation of 10 and subsequent acetylation, gave adenosyl glucoside 22. Protective group manipulations followed by phosphorylation furnished, after deprotection, homogeneous adenophostin A (2) in a high overall yield.

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

Synthesis of polysaccharides with 1,2-cis-glycosidic linkages by trityl-thiocyanate polycondensation. Stereoregular α-(1-6)-D-glucan

The completely stereoregular polysaccharide, α-(1-6)-D-glucan, has been synthesised using a new highly stereospecific type of polycondensation process - trityl-thiocyanate polycondensation.