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31
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85037505838
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note
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2O (3 equiv) instead of BzCl in the aforementioned acylation step furnished the corresponding acetylated derivatives smoothly.
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32
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85037505971
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note
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We cannot give an unbeatable explanation for this regioselectivity. We found that the orientation of anomeric oxygen or sulfur atom is critical to the reaction outcomes. Generally, α-D-manno-, β-D-gluco- and β-D-galactopyranosides gave 3,6-disubstitutes products. Interestingly, α-D-glucopyranosides generate 2,6-disubstitutes while α-D-galactopyranosides gave 2,6- and 3,6-disubstituted mixtures.
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85037495957
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note
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3CO).
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34
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36
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85037501116
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note
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We tried coupling reaction of 17 with 20 on small scale (around 100 mg of reactants) and disaccharide acceptor 21 was obtained in 4 h without adding extra TMSOTf. The same reaction condition was not suitable for larger reaction scale, thus more TMSOTf or trifluoroacetic acid was added into the reaction flask when TLC showed the first coupling reaction finished.
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For "one-pot glycosylation" see (a) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294.
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