Use of Furanoid Glycals in Oligosaccharide Synthesis

Article abstract of DOI:10.1055/s-1997-5756

Furanoid glycals 3, 4 and 9, containing a 3-O-silyl protecting group, are readily epoxidized with DMD to give the respective shelf-stable α-1,2-anhydrofuranoses 7, 8 and 10. The latter oxiranes react smoothly and stereoselectively under the agency of ZnCl₂ with a variety of primary and allylic secondary glycosyl acceptors (e.g. 1, 11-13) resulting in the exclusive formation of β-linked disaccharides (e.g. 14-18) in yields comparable to those obtained starting from 1,2-anhydropyranoses. Furthermore, the dimeric glucofuranoside 18 was transformed into the corresponding 2′-deoxyfuranoside 20, the β-mannofuranoside 21 and the (1→2)-branched furanoside 22.