Collect. Czech. Chem. Commun.
2006, 71, 311-336
https://doi.org/10.1135/cccc20060311
1,6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone
Miloš Buděšínskýa,*, Jana Polákováb, Michaela Hamerníkovác, Ivana Císařovád, Tomáš Trnkab and Miloslav Černýb
a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Department of Organic Chemistry, Faculty of Science, Charles University, 128 40 Prague, Czech Republic
c Department of Biophysics and Physical Chemistry, Charles University, 500 05 Hradec Králové, Czech Republic
d Department of Inorganic Chemistry, Faculty of Science, Charles University, 128 40 Prague, Czech Republic
Abstract
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.
Keywords: Thio sugars; Anhydro sugars; Carbohydrates; Sulfoxides; Sulfones; Conformation analysis; Pummerer rearrangement; NMR spectroscopy; Magnetic anisotropy of sulfinyl group; X-Ray diffraction.
References: 58 live references.
