Journal of the American Chemical Society, Vol.117, No.21, 5701-5711, 1995
Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Le(Y) and Le(B) Blood-Group Determinants and of H-Type-I and H-Type-II Oligosaccharides
The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).
Keywords:SIALYL-LEWIS-X;TRIFLATE MEDIATED GLYCOSIDATIONS;ANION-EXCHANGE CHROMATOGRAPHY;GROUP ANTIGENIC DETERMINANT;HUMAN ADENOCARCINOMA;MOLECULAR RECOGNITION;CHEMICAL SYNTHESIS;STEREOSELECTIVE SYNTHESIS;CARBOHYDRATE LIGAND;MONOCLONAL-ANTIBODY