Improved synthesis of 1,4-dideoxy-1,4-imino-d-galactitol, an inhibitor of E. coli K12 UDP-Gal mutase and mycobacterial galactan biosynthesis

The E. Coli K12 UDP-Gal mutase inhibitor was prepared from d-glucose in 5 steps (42% overall yield). The 4-azido galactose derivative , leading to , was formed by treatment of galactose dithioacetal with mercuric oxide and mercuric chloride in acetone. To obtain , acetal was tosylated or triflated and treated with NaN3.