213459-71-3

Upstream product

• 100-39-0 benzyl bromide 
• 172146-95-1 ethyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 

Downstream Products

• 213459-73-5 5-azidopentyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 1453085-85-2 ethyl (2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranosyl)-(1→6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 213459-90-6 C₅₈H₇₈N₄O₁₃Si₂ 
• 213459-92-8 Acetic acid (2R,3S,4S,5R,6S)-6-(5-azido-pentyloxy)-5-benzyloxy-2-benzyloxymethyl-4-[(2S,3R,4R,5S,6R)-6-benzyloxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl ester 
• 213459-77-9 5-azidopentyl 4-O-acetyl-2,6-di-O-benzyl-α-D-galactopyranoside 
• 213459-76-8 5-azidopentyl 2,6-di-O-benzyl-α-D-galactopyranoside 
• 419549-76-1 5-azidopentyl (4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-77-2 5-azidopentyl (3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-70-5 5-azidopentyl (4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-71-6 5-azidopentyl (3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 419549-59-0 Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester 
• 419549-61-4 5-azidopentyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 369386-67-4 ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 573699-48-6 ethyl 2,6-di-O-benzyl-3,4-O-endo-benzylidene-1-thio-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of the spacer-containing β-D-GalpNAc-(1 →4)-β-D-GlcpNAc-(1→3)-α-D-Galp moiety, representing the non-fucosylated backbone trisaccharide of the glycocalyx glycan of the parasite Schistosoma mansoni

The chemical synthesis of β-D-GalpNAc-(1→4)-β-D-GlcpNAc-(1→3)-α-D-Galp-(1→O)-(CH2)5NH2 is described. This structure represents the nonfucosylated backbone trisaccharide of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni. Synthesis of the trisaccharide was achieved via a stepwise coupling approach. 5-Azidopentyl 4-O-acetyl-2,6-di-O-benzyl-α-D-galactopyranoside was condensed with ethyl 6-O-benzyl-2-deoxy-3,4-di-O-dimethylisopropylsilyl-2-phthalimido- 1-thio-β-D-glucopyranoside, using N-iodosuccinimide and silver trifluoromethanesulfonate as a catalyst system, followed by the removal of the silyl ether groups to afford a disaccharide acceptor. Coupling of ethyl 4,6-di-O-acetyl-3-O-allyloxycarbonyl-2-deoxy-2- phthalimido-1-thio-β-D-galactopyranoside to the disaccharide acceptor, using methylsulfenyl bromide and silver trifluoromethanesulfonate as a catalyst system, gave a protected trisaccharide. Deprotection of this compound yielded the target structure.

Synthesis of a hexasaccharide corresponding to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction in vitro

The synthesis of hexasaccharide 1, [galβ(1-4)GlcNAc[6OSO3]β(1-3)Galβ(1-4)GlcNAcβ(1-3)Galβ(1-3)GalNA cα-O(CH2)3NH2], which corresponds to a porcine zona pellucida fragment that inhibits porcine sperm-oocyte interaction, is described. Compound 1 was obtained from fully protected hexasaccharide 2, which was in turn constructed from protected Galβ(1-3)GalNAc disaccharide 5, containing an α-linked 3-azidopropyl spacer, and from lactosamine derivatives 3 and 4. Disaccharide 3 and 4 were prepared by coupling of selenophenyl glycoside 6 with glycosyl acceptors containing anomeric thioethyl groups. NIS/TfOH promoted coupling of disaccharide 4 with 5 afforded 29, which was transformed into the tetrasaccharide acceptor 30 by selective removal of the levulinoyl group. Glycosylation of 30 with 3 afforded protected hexasaccharide 2. Removal of the phthalimido groups, acetylation, followed by selective removal of the allyl group and sulphation, and finally complete deprotection afforded hexasaccharide 1.