215722-06-8

Upstream product

• 215721-98-5 methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-3-O-tert-butyldiphenylsilyl-1-thio-α-D-mannopyranoside 
• 215721-96-3 methyl 4,6-O-cyclohexylidene-2,3-O-p-methoxybenzylidene-1-thio-α-D-manopyranoside 
• 215721-97-4 methyl 4,6-O-cyclohexylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 
• 215721-95-2 methyl 4,6-O-cyclohexylidene-1-thio-α-D-mannopyranoside 
• 80734-76-5 methyl 1-thio-α-D-mannopyranoside 
• 64550-71-6 methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 77-76-9 2,2-dimethoxy-propane 

Relevant academic research and scientific papers

Highly optimized β-mannosylation via p-methoxybenzyl assisted intramolecular aglycon delivery

Highly efficient and stereoselective β-mannosylation was achieved by using mannosyl thioglycosides 5 and 19. Intramolecular aglycon delivery (IAD) from mixed acetal 12, 15 and 20, obtainable by oxidative coupling of aglycon onto mannosyl thio-glycosides which carry p-methoxybenzyl (PMB) group at C-2 position, was performed by the action of MeOSO2CF3 to afford β-mannosides 13/16/21. It is to be noted that efficiency of IAD was substantially improved by changing the protecting group at the 4- and 6- positions from previously utilized benzylidene to cyclohexylidene (5) or TIPDS (19) group. As a result, it is now possible to perform the β-manno glycosylation in a highly optimized manner to afford di- and trisaccharides with a backbone structure corresponding to asparagine-linked oligosaccharides in 75-85% yield as single stereoisomers.