Pyridine → 2'-Deoxy-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}cytidine

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In one embodiment, 5′-O-DMTR-N4-FMOC-2′-deoxycytidine was prepared according to the following protocol. 30 g (37.9 mmol) of 2′-deoxycytidine hydrochloride were silylated with trimethylchlorosilane (75 ml) in pyridine(160 ml), followed by treatment with fluorenylmethoxycarbonyl chloride (33 g, 128 mmol). After hydrolysis with H2O (300 ml) and extraction with AcOEt/H2O, the N4-FMOC-2′-deoxycytidine was obtained in a 97% yield (49.5 g) as a colorless powder.

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