42891-46-3

Upstream product

• 62-53-3 aniline 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 98-80-6 phenylboronic acid 
• 3945-14-0 tetra-O-acetyl-N-phenyl-α-D-glucopyranosylamine 
• 492-61-5 β-D-glucose 
• 4132-46-1 phenyl 1-amino-β-D-glucopyranoside 

Downstream Products

• 1108180-48-8 C₃₄H₃₈NO₁₁P 

Relevant academic research and scientific papers

Stereoselective copper-catalyzed Chan-Lam-Evans N-arylation of glucosamines with arylboronic acids at room temperature

An efficient and practical N-arylation of glycosylamines with substituted aryl boronic acids has been established. Using Cu(OAc)2 and pyridine at room temperature under air atmosphere, the protocol proved to be general, and a variety of aryl N-glycosides have been prepared in good to excellent yields with exclusive β selectivity.

Synthesis and antiproliferative activity of selenoindirubins and selenoindirubin-N-glycosides

Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated s

Is There a Generalized Reverse Anomeric Effect? Substituent and Solvent Effects on the Configurational Equilibria of Neutral and Protonated N-Arylglucopyranosylamines and N-Aryl-5-thioglucopyranosylamines

The effects of substitution and solvent on the configurational equilibria of neutral and protonated N-(4-Y-substituted-phenyl) peracetylated 5-thioglucopyranosylamines (Y = OMe, H, CF3, NO2) 1-4 and N-(4-Y-substituted-phenyl) peracetylated glucopyranosylamines (Y = OMe, H, NO2) 9-11 are described. The configurational equilibria were determined by direct integration of the resonances of the individual isomers in the 1H NMR spectra after equilibration of both α- and β-isomers. The equilibrations of the neutral compounds 1-4 in CD3OD, CD3NO2, and (CD3)2CO were achieved by HgCl2 catalysis and those of the neutral compounds 9-11 in CD2Cl2 and CD3OD by triflic acid catalysis. The equilibrations of the protonated compounds in both the sulfur series (solvents, CD3OD, CD3NO2, (CD3)2CO, CDCl3, and CD2Cl2) and oxygen series (solvents, CD2Cl2 and CD3OD) were achieved with triflic acid. The substituent and solvent effects on the equilibria are discussed in terms of steric and electrostatic effects and orbital interactions associated with the endo-anomeric effect. A generalized reverse anomeric effect does not exist in neutral or protonated N-aryl-5-thioglucopyranosylamines and N-arylglucopyranosylamines. The anomeric effect ranges from 0.85 kcal mol-1 in 2 to 1.54 kcal mol-1 in 10. The compounds 1-4 and 9-11 show an enhanced endoanomeric effect upon protonation, ranging from 1.73 kcal mol-1 in 2 to 2.57 kcal mol-1 in 10. We estimate the increase in the anomeric effect upon protonation of 10 to be approximately 1.0 kcal mol-1. However, this effect is offset by steric effects due to the associated counterion which we estimate to be approximately 1.2 kcal mol-1. The values of Keq(axial-equatorial) in protonated 1-4 increase in the order OMe 3 2, in agreement with the dominance of steric effects (due to the counterion) over the endo-anomeric effect. The values of Keq(axial-equatorial) in protonated 9-11 show the trend OMe > H 2 that is explained by the balance of the endo-anomeric effect and steric effects in the individual compounds. The trends in the values of the C1-H1 coupling constants for 1-4 and the corresponding deacetylated compounds 5-8 as a function of substituent and α- or β-configuration are discussed in terms of the Perlin effect and the interplay of the endo- and exo-anomeric effects.