From lactose towards a novel galactosylated cyclooctenone.
Lactose was converted into a disaccharide precursor incorporating an allyl vinyl ether substructure within the glucose residue by vinylation, regioselective silylation, tosylation and subsequent elimination. The thermal Claisen rearrangement led to a novel galactosylated cyclooctenone exhibiting a boat-chair conformation.
Jürs
Stefan
S
Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany.
Thiem
Joachim
J
D002236:Carbohydrate Conformation; D034242:Cyclooctanes / Q000138:chemical synthesis* / Q000737:chemistry*; D005690:Galactose / Q000737:chemistry; D007785:Lactose / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure
D034242:Cyclooctanes; D007785:Lactose; D005690:Galactose