1005004-04-5Relevant articles and documents
First synthesis of 4a-carba-β-d-galactofuranose
Frigell, Jens,Cumpstey, Ian
, p. 9073 - 9076 (2007)
The synthesis of 4a-carba-β-d-galactofuranose is described starting from diacetone glucose. The key ring-closure step was carried out by metathesis to form a cyclopentene. Catalytic hydrogenation of the C{double bond, long}C double bond gave the galacto configured saturated carbahexofuranose with excellent diastereoselectivity.
Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives
Frigell, Jens,Eriksson, Lars,Cumpstey, Ian
experimental part, p. 1277 - 1290 (2011/07/09)
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. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a β-galacto configured C-1 thioether.