Pyridine, hydrofluoride (1:1) → Benzyloxymethyl-3'-O-benzoylthymidine

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Reaction Steps

The silyl ether 4 (96.0 g, 136.4 mmol) in THF (600 mL) was treated with hydrogen fluoride-pyridine (70% HF in pyridine, 30 mL) at 0° C. for 4 h under a N2 atmosphere. The resultant mixture was diluted with AcOEt (600 mL) and washed with H2O (2×300 mL). the organic layer was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by silica gel column chromatography (CH2 Cl2 /AcOEt 10:1) to give 61.6 g (97%) of 5 as a white solid. Rf (CH2Cl2 /AcOEt 10:1) 0.29.

Provenance & Evidence