895153-23-8

Basic information

• Product Name: N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide
• Synonyms: N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide
• CAS NO: 895153-23-8
• Molecular Weight: 302.308
• Mol File: 895153-23-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide(895153-23-8)
• EPA Substance Registry System: N-(tert-butoxycarbonyl)-4-nitrobenzenesulfonamide(895153-23-8)

Safety Data

• Hazardous Substances Data: 895153-23-8(Hazardous Substances Data)

Upstream product

• 6325-93-5 p-nitrobenzenesulfonamide 
• 24608-52-4 tert-butyl chloroformate 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 895153-25-0 C₁₇H₂₄N₂O₆SSi 
• 1300749-80-7 N-(but-2-ynyl)-p-nitrobenzenesulfonamide 
• 1361181-58-9 C₁₉H₁₈N₂O₄S 
• 1361181-65-8 C₁₉H₁₈N₂O₄S 
• 492440-30-9 (S)-1-(4-Nitro-benzenesulfonyl)-4-[1-trimethylsilanyl-meth-(Z)-ylidene]-2-vinyl-pyrrolidine 
• 492440-06-9 4-nitro-N-(4-trimethylsilanyl-but-3-ynyl)-benzenesulfonamide 
• 492440-28-5 4-nitro-N-(3-trimethylsilanyl-prop-2-ynyl)-benzenesulfonamide 
• 895153-63-6 C₂₅H₃₂N₂O₆SSi 

Relevant articles and documents

DirectN-glycosylation of tosyl and nosyl carbamates with trichloroacetimidate donors

Under catalyst and additive-free conditions, a convenient and highly efficient eco-friendly method for the stereoselective synthesis ofN-glycofuranosyl and glycofuranosyl sulfonamides has been developed. The two-component reaction of glycofuranosyl trichloroacetimidates with a wide range of tosyl and nosyl carbamate acceptors having varying pKa-values including non-sugar-, and sugar-derived carbamates as well as amino acid-derived carbamates, proceeded smoothly with good yield and β-stereoselectivity. In addition, the selective deprotection ofN-carbamates andN-sulfonyl groups of theN-glycoside functioning as orthogonal protective groups was performed for further functionalization of theN-glycosides.

Self-promoted and stereospecific formation of N-glycosides

A stereoselective and self-promoted glycosylation for the synthesis of various N-glycosides and glycosyl sulfonamides from trichloroacetimidates is presented. No additional catalysts or promoters are needed in what is essentially a two-component reaction. When α-glucosyl trichloroacetimidates are employed, the reaction resulted in the stereospecific formation of the corresponding β-N-glucosides in high yields at ambient conditions. On the other hand, when equatorial glucosyl donors were used, the stereospecificity decreased and resulted in a mixture of anomers. By NMR-studies, it was concluded that this decrease in stereospecificity was due to an, until now, unpresented anomerization of the trichloroacetimidate under the very mildly acidic conditions. The mechanism and kinetics of the glycosylations have been studied by NMR-experiments, which gave an insight into the activation of trichloroacetimidates, suggesting an SNi-like mechanism involving ion pairs. The scope of glycosyl donors and sulfonamides was found to be very broad including popular N-protective groups and common glycosyl donors of various reactivity. Peracetylated GlcNAc trichloroacetimidate could be used without the need for any promotors or additives and a tyrosine side chain was glycosylated as an N-glycosyl carbamate. The N-carbamates and the N-sulfonyl groups functioned as orthogonal protective groups of the N-glycoside and hence allowed further N-functionalization without risking mutarotation of the N-glycoside. The N-glycosylation was also performed on a gram scale, without a drop in stereoselectivity nor yield.

Enantioselective IrI-catalyzed carbocyclization of 1,6-enynes by the chiral counterion strategy

Enantioenriched bicyclo[4.1.0]hept-2-enes were synthesized by Ir I-catalyzed carbocyclization of 1,6-enynes. No chiral ligands were used, CO and PPh3 were the only ligands bound to iridium. Instead, the stereochemical information was