1206101-97-4

Upstream product

• 1279013-85-2 5,6-O-isopropylidene-4a-carba-β-D-galactofuranose 
• 1279013-87-4 1,2,3-tri-O-benzyl-5,6-O-isopropylidene-4a-carba-β-D-galactofuranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 1187444-88-7 1,2,3,6-tetra-O-benzyl-4a-carba-β-D-galactofuranose 
• 1187445-10-8 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->5)-1,2,3,6-tetra-O-benzyl-4a-carba-β-D-galactofuranose 
• 1187445-22-2 2-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->5)-1,2,3,6-tetra-O-benzyl-4a-carba-β-D-galactofuranose 

Relevant academic research and scientific papers

Carbasugar analogues of galactofuranosides: Pseudodisaccharide mimics of fragments of mycobacterial arabinogalactan

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

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.