Ethyl Acetate → HCID 2723959, compound

Participants

Reaction Steps

After adding 0.5 M NaOMe (222.7 mL, 111.0 mmol, 1 eq.) to the allyl glycoside 76 (47.5 g, 111.0 mmol) in solution in MeOH (150 mL), the reaction mixture is stirred for 2 h and its development is monitored by TLC (Chex/EtOAc, 7/3). After observing the disappearance of 76 (Rf=0.6) and the appearance of a more polar product (Rf=0.35), the reaction mixture is neutralized by adding DOWEX (H+) ion-exchange resin, then filtered on a frit. The resin is washed with DCM/MeOH mixture and the solvents are evaporated. The yellow oil obtained is purified by silica gel chromatography (Chex/EtOAc, 8/2→7/3) to give the alcohol 58 in the form of a colorless oil (39.2 g, 92% or 61% starting from commercial L-rhamnose 27).

Provenance & Evidence