191037-58-8

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 102816-24-0 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranosyl azide 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 102816-23-9 2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 

Downstream Products

• 1404438-26-1 C₂₂H₁₉F₃N₄O₈S 
• 182923-92-8 3-O-benzyl-2-deoxy-6-O-(p-methoxyphenyl)-2-phthalimido-β-D-glucopyranosyl azide 
• 191037-60-2 4,6-O-benzylidene-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 218961-16-1 O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)-(1->6)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 
• 218961-14-9 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 

Relevant academic research and scientific papers

One-Pot Glycosylation Strategy Assisted by Ion Mobility-Mass Spectrometry Analysis toward the Synthesis of N-Linked Oligosaccharides

N-Glycans are major constituents of several cellular glycoproteins. One-pot strategies for the synthesis of N-glycans are crucial for the rapid generation of pure samples to determine their biological functions. Herein, we describe a double one-pot strategy for the synthesis of N-glycans assisted by an IM-MS analysis approach for rapid screening of optimized glycosylation reaction conditions. This research includes triflate-mediated direct β-mannosylation and tandem glycosylation in a one-pot strategy for the synthesis of the challenging N-linked trisaccharide core β-5. Furthermore, a one-pot sequential glycosylation of the N-linked trisaccharide core 7 furnishes diverse high-mannose type N-glycans with excellent stereo- and regioselectivities. In particular, ion mobility-mass spectrometry-based quantitative analysis is applied to identify the stereo- and regioselective outcomes of the crude reaction mixtures to develop a highly efficient one-pot protocol.

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

p-Methoxybenzylidene-tethered β-mannosylation for stereoselective synthesis of asparagine-linked glycan chains

One of the main obstacles in the chemical synthesis of Asn-linked glycoprotein oligosaccharides has been the formation of β-manno glycoside linked to the 4 position of N-acetylglucosamine. Addressing this fundamental problem, we previously developed the u