Efficient method for the one-pot azidation of alcohols using bis(p-nitrophenyl) phosphorazidate

Synthesis of novel N-glycoside derivatives via CuSCN-catalyzed reactions and their SGLT2 inhibition activities

“…Under the optimized reaction conditions, the substrate scope of this coupling reaction was examined. As displayed in Table 2, for carbohydrate azides, glucosyl azide 1a, galactosyl azide 1b, 21 and aminoglucosyl azide 1e (see Electronic Supplementary data) performed the reaction smoothly to generate the fully fused-triazole-N-glycosides with high selectivity (entries 1, 2, 5), while mannosyl azide 1c 22 and lactosyl azide 1f 16 just showed moderate selectivity (entries 3 and 7). The fully fused-triazole-N-riboside 3d was also obtained from ribosyl azide 1d 23 in this way (entry 4).…”

Racemization-free synthesis of atropisomeric 1-phenylpyrrole based diamines using diphenylphosphoryl azide

“…17,18 Diphenylphosphoryl azide (DPPA) is also a suitable reagent for modified Curtius reactions. [18][19][20][21][22][23][24][25] In addition, DPPA proved to be highly efficient for racemization-free peptide synthesis, 26 azidation of alcohols, 27 decarbonylation of aldehydes, 28 and the synthesis of oxazoles 29 and thiol esters 30 . Optically active amino alcohols are of great scientific interest; 31,32 the diamines and their derivatives are also widely used as excellent bifunctional ligands and organocatalysts.…”

Azidation of polyesters having pendent functionalities by using NaN3 or DPPA–DBU and photo-crosslinking of the azidopolyesters

“…Azidation of polyesters containing pendent hydroxyl groups by using the DPPA-DBU method Shioiri et al 16 have discovered that p-NO 2 DPPA, prepared easily by nitration of DPPA, 20 in combination with DBU is quite useful and efficient in directly converting alcohols into azides. Following this protocol of the DPPA-DBU method, we converted the pendent hydroxyl groups of the polyesters into azides using p-NO 2 DPPA and DBU.…”

“…1,4-Butanediol (1,4-BD) and 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU) were obtained from Tokyo Kasei Co. (Tokyo, Japan). Scandium trifluoromethanesulfonate (Sc(OTf) 3 ), sodium azide (NaN 3 ) and bis(p-nitrophenyl) azidophosphonate (p-NO 2 DPPA) 16 were purchased from Wako Pure Chemical (Osaka, Japan). 2-Bromoadipic acid (BAA) 17 was prepared in our laboratory.…”