Publikation: N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors
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Journal of Carbohydrate Chemistry. 2010, 29(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673
Zusammenfassung
Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the β-anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).
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540 Chemie
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Carbohydrates, Glycosidation, N-Aryl-O-glycosyl haloacetimidates, Synthesis, O-Imidoylation
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HUCHEL, Uschi, Pallavi TIWARI, Richard R. SCHMIDT, 2010. N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors. In: Journal of Carbohydrate Chemistry. 2010, 29(2), pp. 61-75. ISSN 0732-8303. eISSN 1532-2327. Available under: doi: 10.1080/07328301003597673BibTex
@article{Huchel2010NAryl-13595,
year={2010},
doi={10.1080/07328301003597673},
title={N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors},
number={2},
volume={29},
issn={0732-8303},
journal={Journal of Carbohydrate Chemistry},
pages={61--75},
author={Huchel, Uschi and Tiwari, Pallavi and Schmidt, Richard R.}
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<dcterms:abstract xml:lang="eng">Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the β-anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).</dcterms:abstract>
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