1404438-31-8

Basic information

• Product Name: C₇₇H₆₉F₃N₆O₂₁S
• CAS NO: 1404438-31-8
• Molecular Weight: 1503.48
• Mol File: 1404438-31-8.mol

Chemical Properties

• CAS DataBase Reference: C₇₇H₆₉F₃N₆O₂₁S(CAS DataBase Reference)
• NIST Chemistry Reference: C₇₇H₆₉F₃N₆O₂₁S(1404438-31-8)
• EPA Substance Registry System: C₇₇H₆₉F₃N₆O₂₁S(1404438-31-8)

Safety Data

• Hazardous Substances Data: 1404438-31-8(Hazardous Substances Data)

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 182924-06-7 4,6-O-benzylidene-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 

Downstream Products

• 1404438-33-0 C₇₀H₆₃N₅O₁₉ 
• 1404438-34-1 4,6-O-benzylidene-2-O-(N-phenylcarbamoyl)-β-D-mannopyranosyl-(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 
• 1404438-35-2 4,6-O-benzylidene-3-O-(N-phenylcarbamoyl)-β-D-mannopyranosyl-(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 

Relevant articles and documents

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