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Extension of the Nef reaction to C-glycosylnitromethanes
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SYSNO ASEP 0040171 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Ostatní články Title Extension of the Nef reaction to C-glycosylnitromethanes Title Rozšíření Nefovy reakce na C-glykosylnitromethany Author(s) Petrušová, M. (SK)
Vojtech, M. (SK)
Pribulová, B. (SK)
Lattová, E. (SK)
Matulová, M. (SK)
Poláková, M. (SK)
BeMiller, J. N. (US)
Křen, Vladimír (MBU-M) RID, ORCID
Petruš, L. (SK)Source Title Carbohydrate Research. - : Elsevier - ISSN 0008-6215
Roč. 34, - (2006), s. 2019-2025Number of pages 7 s. Language eng - English Country NL - Netherlands Keywords nef reaction ; anhydronitroalditol ; glycosylnitromethane Subject RIV EE - Microbiology, Virology CEZ AV0Z50200510 - MBU-M (2005-2011) Annotation Acid-catalysed methanolysis of 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-l-arabino-hex-1-enitol proceeds via a cascade set of consecutive reactions resulting in its regiospecific conversion to a mixture of alfa- and beta-C-l-arabinofuranosylmethanal dimethyl acetals and a mixed internal methyl acetal. Structures of the final products of the overall process provide unique evidence that a kinetically controlled, five-membered-ring closure precedes a six-membered-ring closure in reversible systems capable of giving both five-membered and six-membered all-sp3-atom rings. Determination of the reaction intermediate enabled extension of the Nef reaction to C-glycosylnitromethanes. Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2007
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