1279013-77-2Relevant academic research and scientific papers
Carbasugar analogues of galactofuranosides: Pseudodisaccharide mimics of fragments of mycobacterial arabinogalactan
Frigell, Jens,Pearcey, Jean A.,Lowary, Todd L.,Cumpstey, Ian
experimental part, p. 1367 - 1375 (2011/04/17)
A partially protected carbasugar analogue of β-galactofuranose was converted into an α-galacto-configured 1,2-epoxide, which was opened by alcohols under Lewis acid catalysis with regioselective attack at C-1 to give β-galacto-configured C-1 ethers. Using OH-5 and OH-6 carbagalactofuranose derivatives as nucleophiles, we synthesised pseudodisaccharide analogues of substructures of the arabinogalactan from M. tuberculosis. The dicarba analogue of the disaccharide Galf(β1→5)Galf was found to moderately inhibit the action of GlfT2 galactofuranosyl transferase from M. tuberculosis.
Synthesis of carbadisaccharide mimics of galactofuranosides
Frigell, Jens,Cumpstey, Ian
body text, p. 5142 - 5144 (2009/12/03)
A partially protected carbagalactofuranose was converted into a 1,2-anhydro derivative. This epoxide was opened with alcohol nucleophiles under Lewis acid catalysis to give β-carbagalactofuranose pseudodisaccharides with excellent regioselectivity.
