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Upstream product

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

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.