Chemistry of O-Silylated Ketene Acetals: Stereocontrolled Synthesis of 2-Deoxy- and 2-Deoxy-2-C-alkyl-erythro-pentoses

Article abstract of DOI:10.1021/jo00238a015

Diastereoselective aldol reactions of 2,3-O-isopropylidene-D-(and L-)-glyceraldehydes (D- and L-2) with ketene silyl acetal 1a occurred in acetonitrile under mild conditions to give the corresponding anti-β-siloxy esters (D- and L-3a) as major products, which were converted to 2-deoxy-D-(and L-) riboses through a few additional steps.The aldol reactions of D-2 with α-monoalkyl-substituted ketene silyl acetals 1c-f proceeded similarly to give all anti-α-alkyl-β-siloxy esters (11a-14a) as major products, which were converted into 2-deoxy-2-C-alkyl-erythro-pentoses (17a,b).