289884-68-0

Upstream product

• 60254-10-6 (o-hydroxyphenyl)diphenylphosphine 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 829-85-6 diphenylphosphane 
• 533-58-4 2-Iodophenol 
• 1079-66-9 chloro-diphenylphosphine 
• 108-95-2 phenol 
• 62815-32-1 methoxymethyl o-diphenylphosphinophenyl ether 
• 824-91-9 O-methoxymethylphenol 

Downstream Products

• 16522-52-4 2-hydroxyphenyldiphenylphosphine oxide 
• 136755-17-4 N-acetyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine 
• 679430-83-2 1-acetamido-2,3,4-tri-O-benzyl-α-L-fucopyranose 
• 3150-34-3 cytidylyl-(3'->5')-[3']cytidylic acid 

Relevant academic research and scientific papers

Traceless Staudinger Ligation to Introduce Chemical Diversity on β-Lactamase Inhibitors of Second Generation

We explored the traceless Staudinger ligation for the functionalization of the C2 position of second generation β-lactamase inhibitors based on a diazabicyclooctane (DBO) scaffold. Our strategy is based on the synthesis of phosphine phenol esters and thei

Phosphine-Mediated Bioconjugation of the 3′-End of RNA

Staudinger ligation is an attractive bio-orthogonal reaction that has been widely used to tag proteins, carbohydrates, and nucleic acids. Here, we explore the traceless variant of the Staudinger ligation for 3′-end modification of oligoribonucleotides. An azido-containing dinucleotide was used to study the ligation. Nine phosphines containing reactive groups, affinity purification tags, or photoswitch probes have been successfully obtained. The corresponding modified dinucleotides were synthesized and characterized by LC/MS. Mechanistic interpretations of the reaction are proposed, in particular, the unprecedented formation of an oxazaphospholane nucleotide derivative, which was favored by the vicinal position of 2′-N3 and 3′-OH functional groups on the terminal ribose has been observed. The post-functionalization of a 24-nt RNA with a photoactivable tag is also reported.

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

A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds

equation presented Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine. This method for the selective formation of an amide bond, which