191037-60-2

Upstream product

• 123212-53-3 ethyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-N-phthalamido-1-thio-β-D-glucopyranoside 
• 102816-24-0 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide 
• 102816-23-9 2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 100-39-0 benzyl bromide 
• 191037-58-8 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 

Downstream Products

• 161315-66-8 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 218961-14-9 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 1404438-26-1 C₂₂H₁₉F₃N₄O₈S 
• 182923-92-8 3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 
• 214467-65-9 O-(-3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 214467-61-5 O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide 

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 fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides

Fully O-benzylated mono-, di- and trisaccharide glycosyl azides representing the reducing terminal of the core structure of N-glycans were synthesized. Totally and partially benzylated thioalkyl glucosamine glycosides were converted into the corresponding