Novel Approach towards C-C-Linked Carbohydrate Dimers via Claisen Rearrangement of a Disaccharide Allyl Ketene Acetal

Novel Approach towards C-C-Linked Carbohydrate Dimers via Claisen Rearrangement of a Disaccharide Allyl Ketene Acetal

ABSTRACT A disaccharide derivative was synthesised by coupling tri-O-benzyl-D-glucal with an allylic sugar alcohol in a glycosyl­oxy­selenation reaction. Subsequent oxidation followed by SYN-elimination of the selenoxide and in situ rearrangement of the intermediate allyl ketene acetal gave novel C-...

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Veröffentlicht in:Synthesis (Stuttgart) 2006-07, Vol.2006 (13), p.2117-2120
Hauptverfasser: Jürs, Stefan, Thiem, Joachim
Format: Artikel
Sprache:eng
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Zusammenfassung:ABSTRACT A disaccharide derivative was synthesised by coupling tri-O-benzyl-D-glucal with an allylic sugar alcohol in a glycosyl­oxy­selenation reaction. Subsequent oxidation followed by SYN-elimination of the selenoxide and in situ rearrangement of the intermediate allyl ketene acetal gave novel C-C-linked saccharide dimers.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-942407