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1 article(s) from Jia, Xiao G

Intramolecular glycosylation

Xiao G. Jia and
Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

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Graphical Abstract

Scheme 1: The mechanistic outline of the intermolecular (a) and intramolecular (b) glycosylation reactions.

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Figure 1: Three general concepts for intramolecular glycosylation reactions.

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Scheme 2: First intramolecular glycosylation using the molecular clamping.

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Scheme 3: Succinoyl as a flexible linker for intramolecular glycosylation of prearranged glycosides.

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Scheme 4: Template-directed cyclo-glycosylation using a phthaloyl linker.

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Scheme 5: Phthaloyl linker-mediated synthesis of branched oligosaccharides via remote glycosidation.

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Scheme 6: Molecular clamping with the phthaloyl linker in the synthesis of α-cyclodextrin.

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Scheme 7: m-Xylylene as a rigid tether for intramolecular glycosylation.

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Scheme 8: Oligosaccharide synthesis using rigid xylylene linkers.

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Scheme 9: Stereo- and regiochemical outcome of peptide-based linkers.

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Scheme 10: Positioning effect of donor and acceptor in peptide templated synthesis.

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Scheme 11: Synthesis of a trisaccharide using a non-symmetrical tether strategy.

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Scheme 12: Effect of ring on glycosylation with a furanose.

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Scheme 13: Rigid BPA template with various linkers.

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Scheme 14: The templated synthesis of maltotriose in complete stereoselectivity.

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Scheme 15: First examples of the IAD.

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Scheme 16: Long range IAD via dimethylsilane.

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Scheme 17: Allyl-mediated tethering strategy in the IAD.

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Scheme 18: IAD using tethering via the 2-naphthylmethyl group.

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Scheme 19: Origin of selectivity in boronic ester mediated IAD.

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Scheme 20: Arylborinic acid approach to the synthesis of β-mannosides.

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Figure 2: Facial selectivity during HAD.

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Scheme 21: Possible mechanisms to explain α and β selectivity in palladium mediated IAD.

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Scheme 22: DISAL as the leaving group that favors the intramolecular glycosylation pathway.

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Scheme 23: Boronic acid as a directing group in the leaving group-based glycosylation method.

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Review

Published 29 Sep 2017

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