1187444-83-2

Upstream product

• 1005004-09-0 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranose 
• 1187444-93-4 3,5,6-tri-O-benzyl-1-O-(p-tolylsulfonyl)-4a-carba-β-D-galactofuranose 
• 1005004-04-5 (2S,4S,5S,6R)-1,2,4-tri-O-benzyl-3-methyleneoct-7-ene-1,2,4,5,6-pentaol 
• 1005004-07-8 1,2-di-O-acetyl-3,5,6-tri-O-benzyl-4a-carba-β-D-xylohex-4(4a)-enofuranose 
• 35958-64-6 3,5,6-Tri-O-benzyl-D-glucofuranose 

Downstream Products

• 1187445-07-3 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->6)-1,2,3,5-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 
• 1187444-98-9 3,5,6-tri-O-benzyl-1-O-ethyl-4a-carba-β-D-galactofuranose 
• 1187445-14-2 C₄₉H₅₄O₁₀ 
• 1187445-01-7 C₃₁H₃₈O₅ 
• 1187445-13-1 methyl 3,5,6-tri-O-benzyl-4a-carba-β-D-galactofuranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 
• 1187445-04-0 C₃₂H₄₀O₅ 
• 1187445-24-4 C₅₁H₅₆O₁₁ 
• 1187445-25-5 C₅₈H₆₄O₁₁ 
• 1314871-77-6 C₆₆H₇₈O₁₃ 
• 1314871-79-8 3,5,6-tri-O-benzyl-1-deoxy-1-S-ethyl-1-thio-4a-carba-β-D-galactofuranose 
• 1187445-15-3 C₅₆H₆₂O₁₀ 
• 1314871-78-7 C₆₃H₇₄O₁₃ 
• 1187445-32-4 3,5,6-tri-O-benzyl-1,2-di-O-ethyl-4a-carba-β-D-galactofuranose 

Relevant academic research and scientific papers

Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-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. 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.

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.