Carbohydrate Research p. 115 - 129 (1992)
Update date:2022-08-03
Topics:
Vogel
Steffan
Ott
Betaneli
Jones oxidation of suitably protected allyl β-D-galactopyranosides and subsequent esterification were 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-GalpA disaccharide was also prepared.
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