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Stereoselectivity in Glycosylation with Deoxofluorinated Glucosazide and Galactosazide Thiodonors

SYSNO ASEP	0504616
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Stereoselectivity in Glycosylation with Deoxofluorinated Glucosazide and Galactosazide Thiodonors
Author(s)	Kurfiřt, Martin (UCHP-M)_{RID, ORCID, SAI} Červenková Šťastná, Lucie (UCHP-M)_{RID, ORCID, SAI} Dračínský, Martin (UOCHB-X)_{RID, ORCID} Müllerová, Monika (UCHP-M)_{RID, ORCID, SAI} Hamala, Vojtěch (UCHP-M)_{RID, SAI, ORCID} Cuřínová, Petra (UCHP-M)_{RID, SAI, ORCID} Karban, Jindřich (UCHP-M)_{RID, ORCID, SAI}
Source Title	Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263 Roč. 84, č. 10 (2019), s. 6405-6431
Number of pages	27 s.
Language	eng - English
Country	US - United States
Keywords	fluorinated carbohydrates ; stereoselectivity ; fluorination ; glycosylation
Subject RIV	CC - Organic Chemistry
OECD category	Organic chemistry
Subject RIV - cooperation	Institute of Organic Chemistry and Biochemistry - Organic Chemistry
R&D Projects	GA17-18203S GA ČR - Czech Science Foundation (CSF)
Method of publishing	Limited access
Institutional support	UCHP-M - RVO:67985858 ; UOCHB-X - RVO:61388963
UT WOS	000468696400038
EID SCOPUS	85065829028
DOI	10.1021/acs.joc.9b00705
Annotation	Control of anomeric stereoselectivity in glycosylation with deoxofluorinated glycosyl donors is critical for assembly of fluorinated oligosaccharides. Here, we report the synthesis of benzylated 3-fluoro and 4-fluoro analogues of phenyl 1-thioglucosazide and galactosazide donors and evaluation of their stereoselectivity in glycosylation of a series of model carbohydrate acceptors using the Tf2O/Ph2SO promoter system. Low-temperature NMR revealed formation of covalent alpha-triflate and both anomers of oxosulfonium triflates under selected glycosylation conditions. This study demonstrates how the stereoselectivity depends on acceptor reactivity and glycosyl donor configuration. Reactive acceptors favor formation of 1,2- trans-beta-glycosides with both d- gluco and d- galacto donors, whereas poorly reactive acceptors favor formation of 1,2- cis-alpha-glycosides with d- galacto donors but are unselective with d- gluco donors.
Workplace	Institute of Chemical Process Fundamentals
Contact	Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227
Year of Publishing	2020
Electronic address	http://hdl.handle.net/11104/0296202

Number of the records: 1