Bernard Shields Moore

Synthesis of tigogenyl β-O-cellobioside heptaacetate and glycoside tetraacetate via Schmidt's trichloroacetimidate method; some new observatons.

Abstract In studying the synthesis of tigogenyl β-O-cellobioside 1 via the trichloroacetimidate method of Schmidt, cesium carbonate was found to be an efficient reagent for the synthesis of peracetylated disacchadde α-trichloroacetimidates. Zinc bromide was superior to BF 3 ·Et 2 O for coupling these disaccharide α-trichloroacetimidates with the steroid tigogenin.

An efficient preparation of tetrahydropyran-(3R)-carboxaldehyde, a key intermediate for the synthesis of a novel 5-lipoxygenase inhibitor.

Abstract A novel process based on the efficient resolution of rac-2 and suitable for preparing kilogram quantities of the chemically sensitive aldehyde tetrahydropyan-3R-carboxaldehyde R-2 of >-98% ee is described.