t-Butylammonium fluoride → 3-Benzyloxymethyl-3'-benzyloxymethylthymidine

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A solution of 3-benzyloxymethyl-3′-benzyloxymethyl-5′-O-tert-butyldiphenylsilylthymidine (20 g, 28 mmol) in THF (200 10 ml) was treated with tert-butyl ammonium fluoride 1M/THF (40 ml, 40 mmol) at room temperature for 16 hrs. The solution was concentrated in vacuo and the resulting oil chromatographed on silica gel (EtOAc/hexane, 7/3→8/2) to afford the product, 10 g (75%). m.p. 83-84° C.; 1H NMR (CDCl3), 1.92 (s, 3H, C5—CH3), 2.20-2.50 (m, 3H, C2′H, C5′OH), 3.73 (dd, 1H, C5′HH), 3.89 (dd, 1H, C5′HH), 4.09 (m, 1H, C4′H), 4.49(m,1H, C3′H) 4.62 (s, 2H, OCH2Ph), 4.70 (s, 2H, OCH2Ph), 4.81 (s, 2H, OCH2O), 5.49 (s,2H, NCH2O), 6.19 (t, 1H, Cl′H), 7.26-7.37 (m, 5H, CH═,ArH). Anal. Calcd. for C26H30N2O7: C, 64.94; H, 6.26; N, 5.75. Found: C, 64.71; H, 6.27; N, 5.81.

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