215722-18-2

Upstream product

• 64550-71-6 methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 
• 69304-37-6 1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane 
• 80734-76-5 methyl 1-thio-α-D-mannopyranoside 
• 215722-13-7 methyl 2,3-O-p-methoxybenzylidene-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-1-thio-α-D-mannopyranoside 
• 215722-15-9 methyl 2-O-p-methoxybenzyl-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-1-thio-α-D-mannopyranoside 
• 215722-12-6 methyl 4,6-O-(1,1,3,3-tetraisopropyldisiloxanylidene)-1-thio-α-D-mannopyranoside 

Downstream Products

• 309929-66-6 p-methoxyphenyl O-[2,3-O-(p-methoxybenzylidene)-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-β-D-mannopyranosyl]-(1-> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of a novel asparagine-linked heptasaccharide structure via p- methoxybenzyl-assisted β-mannosylation

Synthesis of a core heptasaccharide asparagine N4-{α-D- mannopyranosyl-(1 → 6)-[(α-D-mannopyranosyl)-(1 → 3)]-[(2-acetamido-2- deoxy-β-D-glucopyranosyl)-(1 → 2)]-(β-D-mannopyranosyl)-(1 → 4)-(2- acetamido-2-deoxy-β-D-glucopyranosyl)-(1 → 4)-[(α-L-fucopyranosyl)-(1 → 6)]-2-acetamido-2-deoxy-β-D-glucopyranosyl}-L-asparagine (1a) found from CHO glycosylation mutant cell LEC 14 is described. The structure of 1a is highly novel in terms of the presence of an extra GlcNAc residue linked to the 2-position of β-linked mannose. The synthesis was performed using p- methoxybenzyl-assisted intramolecular aglycon delivery as the key transformation. 4,6-O-TIDPS-protected thiomannoside methyl 2-O-p-me thoxybenzyl-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-3-O- trimethylsilyl-1-thio-α-D-mannopyranoside was adopted for this particular purpose, which afforded β-mannoside p-methoxyphenyl 2,3-O-(p- methoxybenzylidene)-4,6-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-β-D- mannopyranosyl-(1 → 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D- glucopyranoside stereoselectively in 75% yield. (C) 2000 Elsevier Science Ltd.

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.