d-Galacturonic acid derivatives as acceptors and donorsin glycosylation reactions

Jones oxidation of suitably protected allyl β- d-galactopyranosides and subsequent esterificationwere reinvestigated. Partial deprotection of the resulting d-galacturonic acid derivatives afforded compounds suitable for transformation into glycosyl acceptors. The synthesis of 2-, 3-, and 4-trityl et...

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Bibliographic Details
Published in:Carbohydrate research 1992-12, Vol.237, p.115-129
Main Authors: Vogel, Christian, Steffan, Wolfram, Ya. Ott, Andrej, Betaneli, Vitali I
Format: Article
Language:English
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Summary:Jones oxidation of suitably protected allyl β- d-galactopyranosides and subsequent esterificationwere reinvestigated. Partial deprotection of the resulting d-galacturonic acid derivatives afforded compounds suitable for transformation into glycosyl acceptors. The synthesis of 2-, 3-, and 4-trityl ethers, relying on efficient differential protecting-group strategies, is described. Trityl-cyanoethylidene condensation of these trityl ethers, leading to the protected disaccharide units β- d-Gal pA-(1 → 2)- d-Gal pA and β- d-Gal pA-(1 → 3)-Gal pA with high stereoselectivity, is demonstrated. A β- d-Gal pA-(1 → 4)- d-Gal pA disaccharide was also prepared.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(92)84237-M