364373-24-0Relevant articles and documents
Convenient new syntheses of R-(+)-5-benzyloxymethyl-5H-furan-2-one- a building block en route to L-nucleosides
Fazio, Fabio,Maliakal, Davis,Schneider, Manfred P.
, p. 1323 - 1328 (2007/10/03)
R-(+)-5-Benzyloxymethyl-5H-furan-2-one (R-(1)) was obtained from commercially available R-(-)-2-benzyloxymethyl oxirane (R-(2)) in two and three steps, respectively. Key steps are a) the nucleophilic ring opening of the oxirane moiety with dianions derived from either PhSeCH2CO2H or PhSCH2CO2H; b) oxidation to the corresponding 1-oxides and c) concomitant or thermally induced syn-elimination. R-(1) was obtained with ≥97% ee and ≥95% ee, respectively.