Extension of the Nef reaction to C-glycosylnitromethanes

0040171 - MBÚ 2007 RIV SIGLE NL eng J - Journal Article
Petrušová, M. - Vojtech, M. - Pribulová, B. - Lattová, E. - Matulová, M. - Poláková, M. - BeMiller, J. N. - Křen, Vladimír - Petruš, L.
Extension of the Nef reaction to C-glycosylnitromethanes.
[Rozšíření Nefovy reakce na C-glykosylnitromethany.]
Carbohydrate Research. Roč. 34, - (2006), s. 2019-2025. ISSN 0008-6215. E-ISSN 1873-426X
Grant - others:XX APVT-51/039802; XX VEGA-2/6129/26
Institutional research plan: CEZ:AV0Z50200510
Keywords : nef reaction * anhydronitroalditol * glycosylnitromethane
Subject RIV: EE - Microbiology, Virology
Impact factor: 1.703, year: 2006

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.

Byla provedena kysele katalysovaná methanolysa 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-l-arabino-hex-1-enitolu probíhající přes kaskádu reakcí resultující v regiospecifickou konversi směsi alfa- a beta-C-l-arabinofuranosylmethanal dimethyl acetalů a směsných methyl acetalů
Permanent Link: http://hdl.handle.net/11104/0133987