Intramolecular glycoside bond formation - A rigid spacer concept for the diastereoselective linkage between glycosyl donor and acceptor

Article abstract of DOI:10.1016/S0040-4039(98)01664-5

α,α-Dibromo-m-xylene gave compounds 5a,b and 7 which contain a glycosyl donor and acceptor moiety. Activation of 5a,b with NIS/TMSOTf as promoter system afforded β(1-4)-linkage leading to 6 as the only monomeric reaction product. Activation of 7 led also to β(1-4)-linkage affording 8 in very high yield.