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Stage #1: C20H24N2O9S; dichloromethylenebisphosphonic acid bis(tri-n-butylammonium) salt In N,N-dimethyl-formamide at 70℃; for 72h;
Stage #2: With acetic acid In water at 95℃;
Stage #3: In water
6 Typical procedure for the preparation of uridine nucleoside 5'-diphosphate derivatives, 6-18, 23
General procedure: To a suspension of uridine derivatives (0.1 mmol, 1 eq) (33-37, 39 and 41) the appropriate diphosphonatebis(tributylammonium) salt (0.2 mmol, 2 eq) dissolved in dry DMF (0.5 mL) was added: bis(tetrabutylammonium)methylene diphosphonate for 6, 9, 12, 16-18 and 23,bis(tributylammonium)dichloromethylene diphosphonate for 7, 10 and 13 and bis(tributylammonium)difluoromethylene diphosphonate for 8, 11 and 14.The resulting solution was stirred at 70 °C for 3 days. The mixture was cooled to RT and water (5 mL) was added and stirred at RT for 20 min. The solvent was freeze-dried and the crude residue dissolved in a mixture of acetic acid (2 mL) and water (0.5 mL) and stirred for 90 min at 95 °C. 24% NH4OH solution was added to neutralize the reaction mixture which was then freeze-dried. The semisolid obtained was chromatographed on an activated Sephadex DEAE-A25 column. The resin was washed with deionized water and loaded with the crude reaction residue dissolved in a minimal volume of water. The separation was monitored by UV detection at 280 nm. A buffer gradient of 800 mL water to 800 mL 0.5 M NH4HCO3 was used.The relevant fractions were pooled and freeze-dried three times to yield a white solid. Final purification was carried out by HPLC, using a semipreparative reverse-phase column. The purity of the nucleotides was evaluated on an analytical reverse-phase column system in two solvent systems (see below). The products, obtained as triethylammonium salts, were generally>95% pure. Finally, the products (dissolved in water) were passed through a CM Sephadex sodium-form ion-exchange resin column and eluted with deionized water to obtain the corresponding sodium salts after freeze-drying.
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