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Issue 13, 2018
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On the generality of the superarmament of glycosyl donors

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Abstract

It was established that 2-O-benzoyl-3,4,6-tri-O-benzyl protected β-SEt, β-SPh and β-SBox glucosyl donors are not superarmed when using the NIS/TfOH promoter system, but instead have a similar reactivity as their classically armed tetra-O-benzyl protected glucosyl counterparts. The β-SBox 2-O-benzoyl-3,4,6-tri-O-benzyl glucosyl donor, however, was found to be superarmed under DMTST activation. Our studies have shown that the increased reactivity of the β-SBox 2-O-benzoyl-3,4,6-tri-O-benzyl glucosyl donor with DMTST activation could be a unique case, and that the high reactivity of glucosyl donors with the 2-O-benzoyl-3,4,6-tri-O-benzyl protection pattern is not general as earlier suggested.

Graphical abstract: On the generality of the superarmament of glycosyl donors

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Publication details

The article was received on 01 Dec 2017, accepted on 15 Feb 2018 and first published on 15 Feb 2018


Article type: Paper
DOI: 10.1039/C7OB02966G
Citation: Org. Biomol. Chem., 2018,16, 2269-2276
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    On the generality of the superarmament of glycosyl donors

    L. T. Poulsen, M. Heuckendorff and H. H. Jensen, Org. Biomol. Chem., 2018, 16, 2269
    DOI: 10.1039/C7OB02966G

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