502181-50-2

Upstream product

• 502181-38-6 phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 
• 20316-77-2 (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 39698-00-5 acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 91109-44-3 3-O-allyl-D-glucopyranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 502181-48-8 phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 

Downstream Products

• 502181-63-7 methyl 3,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 502181-59-1 methyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-benzyl-(R)-4,6-O-benzylidene-α-D-mannopyranoside 
• 502181-52-4 phenyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-seleno-β-D-glucopyranoside 

Relevant academic research and scientific papers

Total synthesis of the Glc3Man N-glycan tetrasaccharide

The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.