Abstract
AbstractWe previously reported that the selective activation of an S‐benzoxazolyl (SBox) sialyl donor over a galactosyl acceptor equipped with a thioethyl anomeric moiety can be performed in high yield but with poor stereoselectivity. To optimize this strategy, which allows the synthesis of complex carbohydrates to be shortened, a range of SBox sialyl donors modified at C‐5 were synthesized and tested. In particular, the combination of the SBox leaving group and an oxazolidinone at C‐4,5 allowed superior stereocontrol in various solvents and at different temperatures. Nearly complete stereoselectivity was obtained in the presence of bismuth(III) triflate in a dichloromethane/tetrahydrofuran (1:1) solvent system.
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