Universal standard reagents. The use of 3-(2,4-dinitroanilino)propanol (DNAP) and 1-(2,4-dinitrophenyl)-4-hydroxypiperidine (DNPP) in glycosylation and selective hydrolysis of ester glucosides

We demonstrate the utility of the new principle of Universal Standard Reagents (USR) in glycosylation of protected sugars and selective hydrolysis of ester glycosides by means of 3-(2,4-dinitroanilinopropanol) (DNAP) and 1- (2,4-dinitrophenyl)-4-hydroxypiperidine (DNPP). Quantitative determination of each individual sugar derivative was carried out using extinction coefficients at (λ)max (~350 nm) on the micromole scale, eliminating the need for specific standards. The selective hydrolysis of β-DNAP-tetra-O- acetyl- and O- aroylglycosides was examined by different O- and N-bases using quantitative assessment by TLC and HPLC. DCI/NH₃ MS of anomers and NMR- spectra of partially acylated glucosides are discussed.