33639-77-9

Upstream product

• 116514-50-2 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 162118-38-9 (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 
• 151909-89-6 1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose 
• 169532-17-6 ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside 
• 74800-94-5 1-O-p-nitrobenzoyl-2,3,4-tri-O-benzyl-β-L-fucopyranose 
• 83562-59-8 1-O-acetyl-2,3,4-tri-O-benzyl-α-L-fucopyranose 
• 131545-02-3 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 

Downstream Products

• 86781-97-7 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 78499-24-8 p-nitrophenyl 2-acetamido-2-deoxy-4,6-O-(p-methoxybenzylidene)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 81561-92-4 phenyl 2-acetamido-3,6-di-O-acetyl-2-deoxy-4-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 70209-57-3 benzyl O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1<*>2)-O-(3-O-benzoyl-4,6-O-benzylidene-3-O-benzoyl-β-D-galactopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 143528-32-9 8-(Methoxycarbonyl)octyl 2,3,4-tri-O-benzyl-α-L-fucopyranoside 
• 143528-22-7 8-(Methoxycarbonyl)octyl 2,3,4-tri-O-benzyl-β-L-fucopyranoside 
• 81561-94-6 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranose 
• 89077-02-1 (S)-2-Benzyloxycarbonylamino-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester 
• 220601-50-3 1-[7-methoxycarbonyl-1-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose 
• 211562-82-2 N-[(2R,4aR,6R,7R,8R,8aS)-6-Allyloxy-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 220601-52-5 1-[1,2,3,4-tetrahydro-1-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose 
• 204588-83-0 1-[7-(tert-butyldimethylsilyloxy)-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose 
• 204588-66-9 1-[7-methoxycarbonyl-1,2,3,4-tetrahydro-1(R,S)-naphthyl]-2,3,4-tri-O-benzyl-α-L-fucopyranose 
• 204588-76-1 1-{7-[3-(benzyloxycarbonyl)propyl]-1,2,3,4-tetrahydro-1(R,S)-naphthyl}-2,3,4-tri-O-benzyl-α-L-fucopyranose 

Relevant academic research and scientific papers

Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions

A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.

Gram scale synthesis of A (type 2) and B (type 2) blood group tetrasaccharides through 1,6-anhydro-N-acetyl-β-D-glucosamine

Gram scale synthesis of A (type 2) and B (type 2) tetrasaccharides in the form of 3-aminopropyl glycosides is proposed starting from 3-O-benzoyl-1,6-anhydro-N-acetylglucosamine. Its galactosylation followed by re-protection gave lactosamine derivative with single free 2′-OH group in total yield 75%. Standard fucosylation and next run of re-protection in total yield 88% gave a trisaccharide Fuc-Gal-anhydroGlcNAc with single free 3′-OH group. Its standard α-galactosylation gave protected B (type 2) tetrasaccharide. For synthesis of correspondent A tetrasaccharide seven different 2-azido-2-deoxygalactosyl (GalN3) donors were tested: 6-O-acetyl-3,4-O-isopropylidene-GalN3 thioglycoside was shown to provide the best yield (89%) and stereoselectivity (α/β = 24:1). Further 1,6-anhydro cycle opening, spacer-arming and complete deprotection resulted in the target 3-aminopropyl glycosides of A (type 2) and B (type 2) tetrasaccharides, yields 87 and 85% correspondingly.

Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A

Two trisaccharides as new sulfonic acid mimetics of the sialyl Lewis A tetrasaccharide were synthesized. The natural sialic acid residue is replaced by a C-sulfonic acid moiety attached to position C-3′ of the lactosamine unit of the mimetics. The l-fucos

From disulfide- to thioether-linked glycoproteins

(Chemical Presented) Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide-linked bioconjugate is a selective and useful method for site-selective protein glycosylation. The phosphine-mediated desulfurization of such glycoconjugates to their reductant-resistant thioether-linked counterparts completes a convergent, site-selective synthesis of thioether-linked glycoproteins (see scheme).

Glycomimetic inhibitors of the PA-IL lectin, PA-IIL lectin or both the lectins from pseudomonas

Compositions and methods are provided related to Pseudomonas bacteria. The compositions and methods may be used for diagnosis and therapy of medical conditions involving infection with Pseudomonas bacteria. Such infections include Pseudomonas aeruginosa i

Synthesis and antibody-binding studies of a series of parasite fuco-oligosaccharides

Complex multifucosylated oligosaccharides are structural elements of glycoprotein and glycolipid subsets of larval, egg, and adult stages of Schistosoma, the parasitic worms that cause schistosomiasis, a serious disease affecting more than 200 million peo

Linkable sialyl lewis x analogs

Disclosed herein is a class of linkable tetrasaccharide compounds that includes the amino phenyl glycoside of sialyl Lewis X (SLeX) and related analogs. These compounds have conjugatable nucleophilic groups, making them useful in preparing mult

Synthesis of fragments of the glycocalyx glycan of the parasite Schistosoma mansoni

The chemical synthesis of α-L-Fucp-(1→3)-β-D-GalpNAc-(1→4)-β-D-GlcpNAc- (1→3)-α-D-GalpO(CH2)5NH2, β-D-GalpNAc-(1→4)-[α-L-Fucp-(1→3)-]β-D-GlcpNAc- (1→3)-α-D-GalpO(CH2)5NH2, and α-L-Fucp-(1→3

The conformational behaviour of fucosyl and carbafucosyl mimetics in the free and in the protein-bound states

The conformational behaviours of fucosyl glycosides bearing a glyceryl aglycon and their corresponding carbafucosyl glycomimetics have been studied both in aqueous solution and when bound to a fucose-specific lectin (Aurelia Aurantia Agglutinnin), using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations. Analogies and differences between the mimetics and the natural compounds have been found.

Synthesis of the Lewis b hexasaccharide and squarate acid-HSA conjugates thereof with various saccharide loadings

The Lewis b hexasaccharide, α-Ll-Fucp-(1 → 2)-β-D-Galp-(1 → 3)-[α-L-Fucp-(1 → 4)]-β-D-GlcpNAc-(1 → 3)-β-D-Galp-(1 → 4)-β-D-Glcp, has been synthesised using a convergent synthesis. Starting from ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-gluc