Allyl dihydroxyacetate → (3S,4S)-1-[(1R)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine

Beteiligte Stoffe

Reaktionsschritte

To a solution of (3S,4S)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine (700 mg) in toluene (7 ml) was added allyl dihydroxyacetate (560 mg), and the mixture was heated under reflux for 3 hours. The solution was washed with water, dried, and evaporated under reduced pressure to give a mixture (903 mg) of (3S,4S)-1-[(1R)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine and (3S,4S)-1-[(1S)-1-(allyloxycarbonyl)-1-hydroxymethyl]-3[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-{(methylthio)thiocarbonyl}ethyl]-2-oxoazetidine.

Herkunft & Nachweise