923980-28-3

Upstream product

• 4984-68-3 1,6-dideoxy-1,6-epithio-β-D-glucopyranose 
• 98-88-4 benzoyl chloride 
• 50-99-7 D-glucose 
• 5115-93-5 2,3,4-tri-O-acetyl-1,6-dideoxy-1,6-epithio-β-D-glucopyranose 
• 923980-23-8 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose 
• 6619-10-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-β-D-glucopyranose 
• 55500-08-8 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-glucopyranosyl bromide 

Relevant academic research and scientific papers

1,6-Anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan) and the corresponding sulfoxides and sulfone

Starting 1,2,3,4-tetra-O-acetyl-6-O-tosyl-β-D-glucopyranose (3) was converted into 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose (6) via intermediate glycosyl bromide 4 and S-thiouronium salt 5. Treatment of compound 6 with sodium methoxide gave 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan 2a). The isomeric sulfoxides 7 and 8 were prepared by selective oxidation of thiolevoglucosan 2a with hydrogen peroxide or 3-chloroperoxybenzoic acid. The structure of new compounds was confirmed by 1H and 13C NMR spectroscopy or by X-ray analysis; magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed.