Phenyl isocyanate → 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-3'-O-phenylcarbamoylguanosine

Participants

Reaction Steps

The THF solution (33 ml) containing 2,6-bis[(4S)-isopropyl-2-oxazoline-2-yl]pyridine (0.06 mmol, 18.1 mg) and copper chloride (II) (0.06 mmol, 10.2 mg) was stirred for a day at room temperature. After the reaction mixture was cooled to −20° C., the THF solution (32 ml) of 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-guanosine (0.60 mmol, 431.8 mg) and the THF solution (1.6 ml) of phenyl isocyanate (0.60 mmol, 71.5 mg) and K2CO3 (0.60 mmol, 82.9 mg) were sequentially added thereto. After the mixture was stirred for 24.5 hours at −20° C., the THF solution (1.6 ml) of phenyl isocyanate (0.60 mmol, 71.5 mg) was added thereto. After the mixture was further stirred for 23.5 hours, the mixture was analyzed with high-performance liquid chromatography. As a result, it was found that 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-2′-O-phenylcarbamoylguanosine and 5′-O-[bis(4-methoxyphenyl)phenylmethyl]-N2-phenoxyacetyl-3′-O-phenylcarbamoylguanosine were produced at the ratio of 99:1, and the transformation ratio of the reaction was not less than 99%.

Provenance & Evidence