1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 86658528, compound

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Reaction Steps

To a solution of (2R,3R,4R,5R)-5-(2-amino-6-methoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol (2, 4 g, 12.8 mmol) in anhydrous pyridine (100 mL) cooled at 0° C. was added DMT-Cl portion-wise under nitrogen. The brown solution was stirred at ambient temperature for 24 hours. The mixture was concentrated under reduced pressure to remove most of solvent and sat. NaHCO3 (20 mL) was added. The mixture was diluted with water (150 mL) and EtOAc (120 mL). The organic layer was separated and washed with water (5×120 mL), brine and dried over Na2SO4. After removal of solvent, the residue was purified via column chromatography (20% EA in hexanes to 80% EA in hexanes) to afford 11.6 g of product, 3, as a white foam solid (quantitative yield). 1H-NMR (DMSO-d6): δ 7.94 (s, 1H), 7.39-7.37 (m, 3 H), 7.26-7.14 (m, 17H), 6.84-6.80 (m, 8H), 5.58 (s, 1H), 4.04 (br, 1H), 3.71-3.70 (m, 14H), 3.68 (m, 1H), 3.48 (br, 2H), 3.20 (d, 1H), 0.88 (br, 3H).

Provenance & Evidence