Water → Udp-Galactose

Participants

Reaction Steps

Dipotassium α-D-galactosyl phosphate (1.0 equivalents, Sigma), containing 5.5 mol H2O, (110 mg, 253 μmol) was converted into the trioctylammonium salt using 110 μL (253 μmol) trioctylamine and reacted with uridine 5'-monophospho morpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt (296 mg, 404 μmol) and 1H-tetrazole (57 mg, 808 μmol) in dry pyridine (1.25 mL) as described for 32. Purification on a Bio-Gel P-2 column (2.5×95 cm), eluated with 250 mM NH4HCO3, and precipitation from H2 O/MeOH/acetone gave 34 (134 mg, 91%) as a white solid after lyophilization (Rf 0.40, 2:1 i-PrOH/1M NH4OAc). The 1H NMR spectral data were in agreement with the published ones (Heidlas et al. J. Org. Chem. 1992, 57, 152-157).

Provenance & Evidence