Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3'-O-phenylcarbamoyladenosine

Participants

Reaction Steps

The THF solution (75 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.15 mmol, 45.2 mg) and copper chloride (II) (0.15 mmol, 25.6 mg) was stirred for a day at room temperature. After the reaction mixture was cooled to −15° C., the THF solution (15 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyladenosine (1.5 mmol, 1.0 g) and the THF solution (15 ml) of phenyl isocyanate (1.5 mmol, 178.7 mg) and K2CO3 (1.5 mmol, 207.3 mg) were added thereto. After the mixture was continuously stirred for 42 hours at −15° C., the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-2′-O-phenylcarbamoyladenosine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N6-benzoyl-3′-O-phenylcarbamoyladenosine were produced at the ratio of 93:7, and the transformation ratio of the reaction was 99%.

Provenance & Evidence