The Four-Carbon Elongation of Aldehydo Sugars Using 2-(Trimethylsiloxy)furan: A Butenolide Route to Higher Monosaccharides

Article abstract of DOI:10.1021/jo00296a001

2-(Trimethylsiloxy)furan is an available nucleophilic four-carbon synthon that reacts with sugar aldehydes and imines in the presence of BF3 etherate, furnishing γ-C-glycosylated butenolides with very high diastereoselection.The title butenolides represent versatile homochiral candidates to be manipulated into higher carbon sugars.