Synthesis of (3R,5S,6R) 2,6-Diacetoxymethylclavam from D-Galactal

Abstract

N- (t-Butyl)dimethylsilyl-2- C: 1 - N- car bony 1 - 2 -deoxy- α-D-galactopyran-osylamine (1) was tritylated and the product was subjected to a glycolic cleavage to give dialdehyde 10. Subsequently, compound 10 was transformed into bromide 14 using standard procedures. The fluoride anion induced cyclization in 14 afforded clavam 15.