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Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride
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SYSNO ASEP 0369111 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride Author(s) Karban, Jindřich (UCHP-M) RID, ORCID, SAI
Císařová, I. (CZ)
Strašák, Tomáš (UCHP-M) RID, ORCID, SAI
Červenková Šťastná, Lucie (UCHP-M) RID, ORCID, SAI
Sýkora, Jan (UCHP-M) RID, ORCID, SAISource Title Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 10, č. 2 (2012), s. 394-403Number of pages 10 s. Language eng - English Country GB - United Kingdom Keywords carbohydrates ; x-ray crystallography ; benzyloxy group Subject RIV CF - Physical ; Theoretical Chemistry R&D Projects IAA400720706 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z40720504 - UCHP-M (2005-2011) UT WOS 000298555700028 DOI 10.1039/c1ob06336g Annotation A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-beta-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge oxygen (D-allo, D-galacto). The major products yielded by the 1,6:2,3-dianhydropyranoses were compounds arising from nucleophilic substitution, with configuration at C4 either retained (D-talo, D-gulo) or inverted (D-manno), or from C6 migration (D-allo). The minor products in the 1,6:2,3-series resulted from migration of the tetrahydropyran oxygen (D-gulo) or the oxirane oxygen (D-manno), or from nucleophilic substitution with retention of configuration (D-manno). The structure of most of the rearranged products was verified by X-ray crystallography. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2012
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