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1 article(s) from Lehmann, Christian

Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size

Patrick Claude,
Christian Lehmann and
Thomas Ziegler

Beilstein J. Org. Chem. 2011, 7, 1609–1619, doi:10.3762/bjoc.7.189

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Graphical Abstract

Figure 1: Schematic representation of the “prearranged-glycoside concept” for intramolecular, ring-closing gl...

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Figure 2: Structures of compounds 1–5.

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Scheme 1: Intramolecular, ring-closing glycosylation of prearranged glycosides 5a–d.

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Scheme 2: Ring opening of compound 6a.

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Figure 3: Intramolecular glycosylation of peptide-tethered mannosides according to Fairbanks [38-40].

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Figure 4: Isolated β(1→3)-glycosidic linkage favored by triad aromatic-stacking interactions (ASI).

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Figure 5: Stereo view of the superposition of β(1→3)-linked disaccharide models of 6a–d in stable triad-ASI c...

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Figure 6: Most-stable product conformations for the cyclo-glycosidation reaction with ring size spacer n = 2 ...

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Figure 7: Most-stable product conformations for the cyclo-glycosidation reaction with ring size spacer n = 3 ...

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Figure 8: Most-stable product conformations for the cyclo-glycosidation reaction with ring size spacer n = 4 ...

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Figure 9: Most-stable product conformations for the cyclo-glycosidation reaction with ring size spacer n = 5 ...

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Figure 10: Canonical stereoelectronic course of the intramolecular glycosylation reaction leading to the α(1→2...

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Figure 11: Unusual stereoelectronic course of the intramolecular glycosylation reaction leading to the β(1→3)-...

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Full Research Paper

Published 01 Dec 2011

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