Publikation: Synthesis of glycosylthiols and reactivity studies
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2011
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The Journal of Organic Chemistry. 2011, 76(18), pp. 7539-7545. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo200624e
Zusammenfassung
The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-Obenzyl- R-D-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the R-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.
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DERE, Ravindra T., Amit KUMAR, Vipin KUMAR, Xiangming ZHU, Richard R. SCHMIDT, 2011. Synthesis of glycosylthiols and reactivity studies. In: The Journal of Organic Chemistry. 2011, 76(18), pp. 7539-7545. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/jo200624eBibTex
@article{Dere2011-09-16Synth-18128,
year={2011},
doi={10.1021/jo200624e},
title={Synthesis of glycosylthiols and reactivity studies},
number={18},
volume={76},
issn={0022-3263},
journal={The Journal of Organic Chemistry},
pages={7539--7545},
author={Dere, Ravindra T. and Kumar, Amit and Kumar, Vipin and Zhu, Xiangming and Schmidt, Richard R.}
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<dcterms:abstract xml:lang="eng">The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-Obenzyl- R-D-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the R-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.</dcterms:abstract>
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