Synthetic methods 50. Universal standard reagents. The use of 3-(2,4-dinitro-anilino)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 Reage nts (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 coeffici ents at lambda(max) (similar to 350 nm) on the micromole scale, eliminating the need for specific standards. The selective hydrolysis of beta-DNAP-tet ra-O-acetyl- and O- aroyl-glycosides was examined by different O- and N-bas es using quantitative assessment by TLC and HPLC. DCI/NH3 MS of anomers and NMR-spectra of partially acylated glucosides are discussed.