1,2:3,4-Di-O-Isopropylidene-a-D-galactohexodialdo-1,5-pyranose and its C-7, C-8, and C-9 homologues react with the title phosphorane in toluene at room temperature to give the corresponding olefins In good yield and variable EIZ selectivity depending on the dialdose employed. The highest numbered terminus of these thiazole-masked alkene sugars is transformed into a dideoxy undecadialdose by a one-pot reduction of the ethylenic double bond and deblocking of the formyl group from the thiazole ring. © 1990, Taylor & Francis Group, LLC. All rights reserved.
Chain-Elongation of Dialdoses Containing the α-Galactopyranosyl Group By A Wittig Reaction With 2-Thiazolylmethylenetriphenylphosphorane. the Thiazole Route to Long-Chain Alkene Sugars
DONDONI, Alessandro;FANTIN, Giancarlo;FOGAGNOLO, Marco;
1990
Abstract
1,2:3,4-Di-O-Isopropylidene-a-D-galactohexodialdo-1,5-pyranose and its C-7, C-8, and C-9 homologues react with the title phosphorane in toluene at room temperature to give the corresponding olefins In good yield and variable EIZ selectivity depending on the dialdose employed. The highest numbered terminus of these thiazole-masked alkene sugars is transformed into a dideoxy undecadialdose by a one-pot reduction of the ethylenic double bond and deblocking of the formyl group from the thiazole ring. © 1990, Taylor & Francis Group, LLC. All rights reserved.File in questo prodotto:
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