Allyl Alcohol → HCID 67541844, compound

Participants

Reaction Conditions

Reaction Steps

TMSOTf (830.0 μL, 4.6 mmol, 0.2 eq.) is added to a solution of allyl alcohol (3.1 mL, 46.0 mmol, 2 eq.) and of donor 1 (13.7 g, 23.0 mmol, 1 eq.) in DCM (160 mL), in the presence of molecular sieve 4 Å (8.9 g), stirred under argon at −78° C. After stirring for 30 min, monitoring by TLC (Tol/EtOAc, 8/2) indicates the disappearance of the donor (Rf=0.5) and the appearance of a new, more polar compound (Rf=0.35). The reaction is stopped by adding triethylamine (1 mL) and then the reaction mixture is filtered and concentrated in a rotary evaporator. The yellow oil obtained is purified by silica gel chromatography (Tol/EtOAc, 9/1→75/25) to obtain the allyl glycoside 18 as a white solid (9.4 g, 83%).

Provenance & Evidence