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Article: Thioglycosylation of 1,2-cis-glycosyl acetates: a long-standing overlooked issue in preparative carbohydrate chemistry

TitleThioglycosylation of 1,2-cis-glycosyl acetates: a long-standing overlooked issue in preparative carbohydrate chemistry
Authors
Xu, CLiu, HLi, X
KeywordsThioglycoside
Lewis-acid catalyzed thioglycosylation
1,2-cis-Glycosyl acetates
Issue Date2011
PublisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/carres
Citation
Carbohydrate Research, 2011, v. 346 n. 9, p. 1149-1153 How to Cite?
DOI: http://dx.doi.org/10.1016/j.carres.2011.03.033
Abstract1,2-cis-Glycosyl acetates with the alpha-configuration were revealed to be very unreactive towards Lewis acid catalyzed thioglycosylations. Optimal and cost-effective conditions for enabling this direct conversion is absent in the literature. Our studies have shown that elevating the reaction temperature with a catalytic amount of BF(3).OEt(2) was more effective than changing Lewis acids with higher acidities to accommodate the low reactivity of alpha-glycosyl acetates. The effect of impurities in stored BF(3).OEt(2) on the reaction is also discussed.
Persistent Identifierhttp://hdl.handle.net/10722/159316
ISSN
0008-6215
2021 Impact Factor: 2.975
2020 SCImago Journal Rankings: 0.465
ISI Accession Number ID
WOS:000291417000009
References
References in Scopus

 

DC FieldValueLanguage
dc.contributor.authorXu, Cen_HK
dc.contributor.authorLiu, Hen_HK
dc.contributor.authorLi, Xen_HK
dc.date.accessioned2012-08-16T05:48:36Z-
dc.date.available2012-08-16T05:48:36Z-
dc.date.issued2011en_HK
dc.identifier.citationCarbohydrate Research, 2011, v. 346 n. 9, p. 1149-1153en_HK
dc.identifier.issn0008-6215en_HK
dc.identifier.urihttp://hdl.handle.net/10722/159316-
dc.description.abstract1,2-cis-Glycosyl acetates with the alpha-configuration were revealed to be very unreactive towards Lewis acid catalyzed thioglycosylations. Optimal and cost-effective conditions for enabling this direct conversion is absent in the literature. Our studies have shown that elevating the reaction temperature with a catalytic amount of BF(3).OEt(2) was more effective than changing Lewis acids with higher acidities to accommodate the low reactivity of alpha-glycosyl acetates. The effect of impurities in stored BF(3).OEt(2) on the reaction is also discussed.en_HK
dc.languageengen_US
dc.publisherPergamon. The Journal's web site is located at http://www.elsevier.com/locate/carresen_HK
dc.relation.ispartofCarbohydrate Researchen_HK
dc.subjectThioglycoside-
dc.subjectLewis-acid catalyzed thioglycosylation-
dc.subject1,2-cis-Glycosyl acetates-
dc.subject.meshAcetates - chemical synthesis - chemistryen_HK
dc.subject.meshCarbohydrate Conformationen_HK
dc.subject.meshGalactosides - chemical synthesis - chemistryen_HK
dc.subject.meshGlucosides - chemical synthesis - chemistryen_HK
dc.subject.meshSulfhydryl Compounds - chemistryen_HK
dc.titleThioglycosylation of 1,2-cis-glycosyl acetates: a long-standing overlooked issue in preparative carbohydrate chemistryen_HK
dc.typeArticleen_HK
dc.identifier.emailLiu, H: liuhan@hku.hken_HK
dc.identifier.emailLi, X: xuechenl@hku.hk-
dc.identifier.authorityLi, X=rp00742en_HK
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1016/j.carres.2011.03.033en_HK
dc.identifier.pmid21524413-
dc.identifier.scopuseid_2-s2.0-79955936548en_HK
dc.identifier.hkuros203772en_US
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-79955936548&selection=ref&src=s&origin=recordpageen_HK
dc.identifier.volume346en_HK
dc.identifier.issue9en_HK
dc.identifier.spage1149en_HK
dc.identifier.epage1153en_HK
dc.identifier.eissn1873-426X-
dc.identifier.isiWOS:000291417000009-
dc.publisher.placeUnited Kingdomen_HK
dc.identifier.scopusauthoridLi, X=24168958800en_HK
dc.identifier.scopusauthoridLiu, H=52164019000en_HK
dc.identifier.scopusauthoridXu, C=52164745400en_HK
dc.identifier.citeulike9181692-
dc.identifier.issnl0008-6215-

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