Tin tetrachloride → HCID 136173388, compound

Participants

Reaction Steps

N-Acetyl Guanosine (108 mg, 0.56 mmol) was suspended in 10 mL anhydrous CH2Cl2. With stirring under nitrogen, BSA (345 mg, 1.4 mmol) was added to the suspension. The mixture was stirred at 80° C. for 2 h and cooled to r.t. Compound 35.14 (200 mg, 0.37 mmol) in 5 mL anhydrous DCE was added to the mixture, followed by SnCl4 (64 mL, 0.55 mmol). The mixture was heated to 65° C. for 6 h and then cooled to r.t., diluted with 50 mL CH2Cl2 and poured onto a mixture of 50 g ice/50 mL saturated Rochelles Salt. The mixture was stirred for another 1 h. The organic layer was separated and the aqueous layer was extracted with 100 mL additional CH2Cl2. The organic extracts were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with 5% MeOH in CH2Cl2 to give compound 35.15 (73 mg, 30% yield).

Provenance & Evidence