Synthesis of glycosylthiols and reactivity studies


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DERE, Ravindra T., Amit KUMAR, Vipin KUMAR, Xiangming ZHU, Richard SCHMIDT, 2011. Synthesis of glycosylthiols and reactivity studies. In: The Journal of Organic Chemistry. 76(18), pp. 7539-7545. ISSN 0022-3263. eISSN 1520-6904

@article{Dere2011-09-16Synth-18128, title={Synthesis of glycosylthiols and reactivity studies}, year={2011}, doi={10.1021/jo200624e}, 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} }

<rdf:RDF xmlns:rdf="" xmlns:bibo="" xmlns:dc="" xmlns:dcterms="" xmlns:xsd="" > <rdf:Description rdf:about=""> <dc:creator>Kumar, Vipin</dc:creator> <dc:contributor>Schmidt, Richard</dc:contributor> <dc:creator>Dere, Ravindra T.</dc:creator> <dcterms:bibliographicCitation>First publ. in: Journal of Organic Chemistry ; 76 (2011), 18. - pp. 7539-7545</dcterms:bibliographicCitation> <dc:contributor>Kumar, Amit</dc:contributor> <dc:creator>Zhu, Xiangming</dc:creator> <dc:rights>deposit-license</dc:rights> <dcterms:issued>2011-09-16</dcterms:issued> <dc:creator>Kumar, Amit</dc:creator> <dc:contributor>Kumar, Vipin</dc:contributor> <dc:language>eng</dc:language> <dc:contributor>Zhu, Xiangming</dc:contributor> <dc:contributor>Dere, Ravindra T.</dc:contributor> <dc:creator>Schmidt, Richard</dc:creator> <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> <dcterms:rights rdf:resource=""/> <dcterms:title>Synthesis of glycosylthiols and reactivity studies</dcterms:title> <dcterms:available rdf:datatype="">2012-06-30T22:25:08Z</dcterms:available> <dc:date rdf:datatype="">2012-02-14T11:58:15Z</dc:date> <bibo:uri rdf:resource=""/> </rdf:Description> </rdf:RDF>

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