309929-66-6

Upstream product

• 215722-18-2 p-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside-methyl 4',6'-O-(1,1,3,3-tetraisopropyl)disiloxanylidene-3'-O-trimethylsilyl-1'-thio-α-D-mannopyranoside-2',4-p-methoxybenzylidene acetal 

Downstream Products

• 309929-69-9 p-methoxyphenyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1-> 3)-4,6-di-tert-butylsilanediyl-β-D-mannopyranosyl-(1-> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 309929-68-8 p-methoxyphenyl 4,6-O-di-tert-butylsilanediyl-β-D-mannopranosyl-(1-> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucpyranoside 
• 309929-67-7 p-methoxyphenyl 2,3-O-p-methoxybenzylidene-β-D-mannopyranosyl-(1-> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Relevant academic research and scientific papers

On the mechanism of p-methoxybenzylidene assisted intramolecular aglycon delivery

p-Methoxybenzylidene-assisted intramolecular aglycon delivery was developed in this laboratory and has been demonstrated to be highly efficient and versatile particularly for the synthesis of complex glycoprotein-related glycans. It was revealed that the reaction course of IAD can be clearly monitored by performing the reaction in an NMR tube. Our results suggest that the nonhydrolytic pathway that converts metastable intermediate 3 to the product is functional. Comparative experiments in the presence and absence of water in the reaction media afforded supporting evidence eliminating the possibility of fortuitous contamination of water under standard IAD conditions.

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.