1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone

Abstract

1,2,3,4-tetra-O-acetyl-6-O-tosyl-b-D-glucopyranose was converted into 2,3,4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose and on reaction with sodium methoxide to 1,6-anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan).

Thiolevoglucosan was used for preparation of isomeric sulfoxides and sulfone. The structure of new compounds was confirmed by NMR and X-ray analysis. Magnetic anisotropy of the sulfinyl and sulfonyl group has been discussed.

Keywords

• thio sugars
• anhydro sugars
• carbohydrates
• sulfoxides
• sulfones
• conformation analysis
• pummerer rearrangement
• NMR spectroscopy
• magnetic anisotropy of sulfinyl group
• X-Ray diffraction