Thymidine → HCID 18658254, compound

Participants

Reaction Steps

To a stirred solution of 3′- cyano-2′,3′-dideoxy-5′-O-trityluridine (0.96 g, 2 mmol), (prepared in a manner equivalent to that of the thymidine analog above) in dry THF (20 ml) under argon, was added a solution of DIBAL-H in toluene (Aldrich) (1M, 4 ml) at −10° C. over a period of 10 min. After 30 mins the reaction was quenched with MeOH (5 ml) at −10° C. The mixture was further stirred at ambient temperature for 30 mins and diluted with CH2Cl2 (25 ml) before concentrating under vacuum. This process was repeated with CH2Cl2 (3×25 ml) in order to remove the residual THF. The residue was purified by flash chromatography on silica gel (25 g). Elution with CH2Cl2 (9:1, v/v) and crystallization from CH2Cl2/MeOH gave 5′-O-trityl-3′-C-formyl-2′,3′-dideoxyuridine (0.53 g, 53%); mp 100° C.; 1H NMR (CDCl3) δ 2.25-2.8 (m, 2, CH2), 3.4 (m, 1, C3′H), 3.45-3.6 (m, 2, C5′CH2), 4.37 (m, 1, C4′H) 5.4 (d, 1, C5H), 6.1 (m, 1, C1′H), 7.2-7.4 (m, 15, C6H5), 7.81 (d, 1, C6H), 7.95 (br s, 1, NH), 9.61 (s, 1, HC═O).

Provenance & Evidence