182923-98-4

Upstream product

• 182923-95-1 3,6-di-O-benzyl-4-O-(chloroacetyl)-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 
• 150-76-5 4-methoxy-phenol 
• 115533-35-2 ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 129519-27-3 2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 
• 182924-27-2 2-((2S,3R,4R,5S,6R)-4-Benzyloxy-2-fluoro-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione 
• 123191-40-2 ethyl 3-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 182923-83-7 Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-fluoro-tetrahydro-pyran-3-yl ester 
• 182923-86-0 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-2-fluoro-5-hydroxy-6-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 123191-43-5 Acetic acid (2R,3S,4R,5R,6S)-2-acetoxymethyl-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yl ester 
• 182923-79-1 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 
• 560129-48-8 ethyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 182923-92-8 3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 
• 182923-89-3 Chloro-acetic acid (2R,3S,4R,5R,6R)-6-azido-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-methoxy-phenoxymethyl)-tetrahydro-pyran-3-yl ester 
• 218961-14-9 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 

Downstream Products

• 182924-04-5 4,6-O-benzylidene-2-O-(chloroacetyl)-3-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 
• 1404438-30-7 C₇₈H₇₁ClN₆O₂₀ 

Relevant academic research and scientific papers

Modular synthesis of core fucosylated N-glycans

A modular synthesis of complex-type N-glycans containing the core fucosyl motif was optimized. The core trisaccharide building block was protected by a methoxyphenyl group for convenient core fucosylation. The trisaccharide was obtained on a large scale from the glycosylation of the corresponding chitobiosyl azide with a glucosyl donor followed by intramolecular inversion. Improved methods were established for the synthesis of the monosaccharide building blocks and for their couplings. The inversion to the β-mannoside was accompanied by previously unnoticed side-reactions resulting in the hydrolytic ring-opening of the iminocarbonate intermediate. The benzylidene-protected core trisaccharide was elongated into a biantennary N-glycan heptasaccharide by two regio- and stereoselective couplings. The final fucosylation also gave some of the β anomer, which could be removed by HPLC to give an α1,6-fucosylated N-glycan octasaccharide. A modular synthesis of core-fucosylated N-glycans was optimized, leading to the biantennary octasaccharide N-glycan A. Several obstacles to the synthesis of functionalized core trisaccharide building block B were overcome, leading to an improved and efficient protocol for β-mannosylation by intramolecular inversion. Copyright

Synthesis of a core-fucosylated, biantennary octasaccharide as a precursor for glycopeptides of complex N-glycans

A convergent synthesis of the biantennary and core-fucosylated octasaccharide 20 (a protected from of A) is described. Octasaccharide 20 is designed to serve as a precursor for dodecasaccharide 1, a complex N-glycan frequently found in glycoproteins of th