Glycerol → HCID 11782182, compound

Participants

Reaction Steps

Propargyl bromide (2.2 ml, 19.7 mmol) and 1,8 diazabicyclo[5.4.0]undec-7-ene (DBU) (2.7 ml, 17.7 mmol) were added to a suspension of 2'-O-methylinosine (5.4 g, 19.0 mmol) in dimethylacetamide (100 ml). The reaction mixture was stirred at room temperature under argon for 18 hours at which time an additional 1 ml of DBU was added. After 6 hours, the reaction solution was evaporated in vacuo to an oil and dried onto 20 g of silica gel. Pure product was isolated by silica gel chromatography with a 2-5% gradient of methanol in chloroform. FABMS (glycerol & methanol) m/z 321 (MH+). 1H-NMR (DMSO-d6): 8.50 (1H,s, H2); 8.41 (1H, s, H8); 5.96 (1H, d, H1'); 5.28 (1H, d, 2'--OH); 5.09 (1H, t, 5'--OH); 4.82 (2H, s, CH2); 4.27 (2H, m, H2', H3'); 3.94 (1H, m, H4'); 3.60 (2H, m, H5', H5"); 3.41 (1H, s, CH).

Provenance & Evidence