Carbasugar analogues of galactofuranosides: β-O-linked derivatives
(English)Manuscript (preprint) (Other academic)
A selectively protected carbasugar analogue of β-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an α-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give β-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides.
carbasugar, galactofuranose, galactofuranoside, tuberculosis, mycobacterium tuberculosis
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-44209OAI: oai:DiVA.org:su-44209DiVA: diva2:360311