177358-27-9

Upstream product

• 123-76-2 levulinic acid 
• 1423018-01-2 C₂₉H₂₈O₈S 
• 210093-48-4 ethyl 2,6-di-O-benzoyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside 
• 194858-02-1 ethyl 2,6-di-O-benzoyl-1-thio-β-D-galactopyranoside 

Downstream Products

• 177358-31-5 3-azidopropyl 3-O-(2,4,6-tri-O-benzoyl-3-O-levulinoyl-β-D-galactopyranosyl)-2-acetylamino-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 

Relevant academic research and scientific papers

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.