Carbasugar analogues of galactofuranosides : β-O-linked derivatives

• 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.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

carbasugar

galactofuranose

galactofuranoside

tuberculosis

mycobacterium tuberculosis

Organic synthesis

Organisk syntes

organisk kemi

Organic Chemistry

Publikations- och innehållstyp

vet (ämneskategori)

ovr (ämneskategori)