116113-13-4

Upstream product

• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 1071226-27-1 methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate 

Relevant academic research and scientific papers

Studies on the sialylation of galactoses with different C-5 modified sialyl donors

Synthetic sialylated glycans provide useful tools to study carbohydrate-mediated biological recognition; however chemical sialylation is the most challenging practice in preparative carbohydrate chemistry, which is often associated with low yields and poor stereoselectivity. Herein, we conducted extensive studies on sialylation with five types of 5-N-modified sialyl donors and four types of galactosyl acceptors. Our studies have shown that a good combination between the donor and the acceptor seems necessary to achieve high yield and stereoselectivity. None of the donors or acceptors showed 'universal' utility toward the sialylation reaction.

SYNTHESE EINES TRISACCHARIDES AUS N-ACETYLNEURAMINSAEURE UND N-ACETYLLACTOSAMIN

The reaction of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate with benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside in the presence of mercury cyanide-mercuri bromide gave a 1:1 mixture of the two anomeric (2->6)linked trisaccharides containing N-acetylneuraminic acid.By chromatography, 22percent of benzyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside and 23percent of the corresponding β-(2->6)-linked isomer could be isolated.A deblocking sequence, consisting of hydrogen sulfide reduction, acetylation, deacetylation, ester hydrolysis and hydrogenolysis led to the deblocked O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose and to the corresponding β-(2->6)-linked compound.