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Issue 26, 2011
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Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

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Abstract

The formation of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose was observed in the gold(I)-catalyzed glycosidation of peracetyl glucopyranosyl ortho-hexynylbenzoate; experiments with substrates bearing deuterium labeled 2-O-acetyl or 4-O-acetyl groups indicated that the orthoacetate was derived from the 4-O-acetyl group, which provided a direct evidence for the remote participation of the 4-O-acyl group in glycosylation.

Graphical abstract: Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-d-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

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Publication details

The article was received on 24 Mar 2011, accepted on 09 May 2011 and first published on 31 May 2011


Article type: Communication
DOI: 10.1039/C1CC11680K
Chem. Commun., 2011,47, 7515-7517

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    Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

    Y. Ma, G. Lian, Y. Li and B. Yu, Chem. Commun., 2011, 47, 7515
    DOI: 10.1039/C1CC11680K

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