Preparation of β-D-Glucopyranosyl Derivatives of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses and Their <sup>1</sup>H and <sup>13</sup>C NMR Spectra

Buděšínský, Miloš; Černý, Miloslav; Černý, Ivan; Sámek, Stanislav; Trnka, Tomáš

doi:10.1135/cccc19950311

CCCC > Archive > 1995, Volume 60 > Issue 2 > p. 311

Preparation of β-D-Glucopyranosyl Derivatives of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses and Their ¹H and ¹³C NMR Spectra

Miloš Buděšínský^a, Miloslav Černý^b, Ivan Černý^a, Stanislav Sámek^b and Tomáš Trnka^b

^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, Charles University, 128 40 Prague 2, Czech Republic

Abstract

The corresponding acetylated and free 2-O- and 4-O-glucosyl derivatives of dianhydrohexoses Ib - VIIb and Ic - VIIc have been obtained by the reactions of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (IX) with 1,6:3,4- and 1,6:2,3-dianhydro-β-D-hexopyranoses (Ia - VIIa). Structure of the products and the effects of glycosylation upon chemical shifts and conformations of the disaccharides prepared have been studied using ¹H and ¹³C NMR spectra.

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Preparation of β-D-Glucopyranosyl Derivatives of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses and Their 1H and 13C NMR Spectra

Abstract

Preparation of β-D-Glucopyranosyl Derivatives of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses and Their ¹H and ¹³C NMR Spectra