- Easy access to C-glycosides from aldonolactones by a Claisen-type chain-extension reaction
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Chain elongated 2,4-diuloses 2, 4, 6, 9-11, 24, 25 were conveniently obtained from the corresponding aldonolactones 1, 3, 5 by their reaction with carbonyl compounds in the presence of sodium hydride. These hemiacetalic products can be transformed into C-
- Csuk, Rene,Kuehn, Martin,Stroehl, Dieter
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p. 1311 - 1322
(2007/10/03)
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- A new route to some enantiomerically pure substituted morpholines from D-ribono- and D-gulono-1,4-lactones
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D-Ribono-1,4-lactone, after acetalation, tritylation, and reduction, leads to a cyclization compound which gave with tosyl chloride 1,4-anhydro-2,3-O-isopropylidene-5-O-trityl-D-ribitol.The latter was transformed (acid hydrolysis, periodate oxidation, reduction, tritylation, and tosylation) into a ditosylated derivative 16, which was cyclized into morpholines by the action of primary amines.Acid hydrolysis, followed by acetylation, gives the (2S)-acetoxymethyl-4-isopropyltetrahydro-1,4-oxazine (21).A similar sequence has been applied to D-gulonolactone to give access to oxazines 33, 34, and 35. Keywords: Synthesis; D-Ribono-1,4-lactone; D-Gulono-1,4-lactone; Morpholine derivatives
- Bennis, Khalil,Calinaud, Pierre,Gelas, Jacques,Ghobsi, Mebrouk
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