136755-17-4

Upstream product

• 74372-91-1 2,3,4,6-tri-O-benzyl-α-D-glucopyranosyl chloride 
• 13435-12-6 N-Trimethylsilylacetamide 
• 134003-35-3 pent-4-enyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 85917-82-4 1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 289884-68-0 acetyl o-diphenylphosphinophenyl ether 
• 136755-16-3 N-acetyl-2,3,4,6-tetra-O-benzyl-N-(benzyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine 

Relevant academic research and scientific papers

Direct Coupling of Amides and Urea to Glycosyl Halides Using Silver Triflate

We herein report the coupling of various amides and ureas to glycosyl halides in the presence of silver triflate at room temperature. A 1:1 mixture of α/β diastereomers was obtained when alkyl/heteroaryl amides and substituted ureas were added to gluco an

Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides

α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4 °C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation and allows retention of configuration at the anomeric carbon. Yields and α-selectivity are high when the reaction is performed in polar aprotic solvents. Removal of the benzyl ether protecting groups is achieved by catalytic hydrogenation. α-Glycosyl amides represent a class of virtually unexplored nonhydrolyzable monosaccharide derivatives that may find a useful application as sugar mimics. Conformational studies by NMR spectroscopy confirm that deprotected α-glycosyl amides in the gluco, galacto, and fuco series retain the normal pyranose conformation of the monosaccharide. The reaction of phosphines 4 with tetra-O-acetyl-glycosyl azides is nonstereoconservative, and β-glycosyl amides are obtained in good yields and with complete stereoselectivity starting from both α and β azides.

Selective synthesis of anomeric α-glycosyl acetamides via intramolecular Staudinger ligation of the α-azides

α-Glycosyl azides can be transformed into the corresponding α-glycosyl acetamides with complete retention of configuration via reduction-acylation (Staudinger ligation) reactions using specifically functionalized phosphines. The α-acetamides of per-O-benz

Application of n-pentenyl glycosides in the regio- and stereo-controlled synthesis of α-linked N-glycopeptides

The N-glycopeptides α-Glc-(1→Asn and α-Glc-(1→6)-β-Glc-(1→6)-α-Glc-(1→Asn have been synthesized efficiently from pent-4-enyl D-glucopyranoside derivatives. The methodology illustrates (a) a novel route for formation of the N-α-D-glucosyl-asparagine link,