Different protecting groups on the glycosyl donor changes the stereoselectivity of the new glycosylation reaction shown in the scheme. Glycosylation of CB 4,6-O-benzylidene-2-deoxyglycoside 1 with secondary alcohol acceptors gave predominantly β-disaccharides 3, whereas the same reaction with CB tri-O-benzyl-2-deoxyglycoside 2 afforded α-disaccharides 4. CB=(2′-carboxy)benzyl.
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Kim et al. (2003) studied this question.
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