Synlett p. 851 - 853 (1997)
Update date:2022-08-04
Topics:
Timmers, Cornelis M.
Verheijen, Jeroen C.
Van Der Marel, Gijsbert A.
Van Boom, Jacobus H.
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.
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Doi:10.1002/chem.201603082
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(1997)