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We 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...