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Modular Synthesis of 5-Substituted Furan-2-yl C-2'-Deoxyribonucleosides and Biaryl Covalent Base-pair Analogues

SYSNO ASEP	0350078
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Modular Synthesis of 5-Substituted Furan-2-yl C-2'-Deoxyribonucleosides and Biaryl Covalent Base-pair Analogues
Author(s)	Bárta, Jan (UOCHB-X) Slavětínská, Lenka (UOCHB-X)_RID Klepetářová, Blanka (UOCHB-X)_{RID, ORCID} Hocek, Michal (UOCHB-X)_{RID, ORCID}
Number of authors	4
Source Title	European Journal of Organic Chemistry - ISSN 1434-193X -, č. 28 (2010), s. 5432-5443
Number of pages	12 s.
Language	eng - English
Country	DE - Germany
Keywords	C-nucleosides ; furans ; C-glycosidation ; cross-coupling reactions
Subject RIV	CC - Organic Chemistry
R&D Projects	LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
	IAA400550902 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000283387900013
DOI	10.1002/ejoc.201000726
Annotation	A modular and efficient synthesis of 5-(hetero)arylfuran C-2'-deoxyribonucleosides was developed. Friedel–Crafts C-glycosidation of 2-bromofuran with toluoyl-protected methyl 2'-deoxyribofuranoside in the presence of BF3·Et2O gave 5- bromofuran C-nucleosides, which were used as key intermediates for Stille or Suzuki coupling with (hetero)arylstannanes or boronic acids to afford a series of 5-(hetero)arylfuran C-nucleosides.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2011

Number of the records: 1