セロビオースのトリチル誘導体(第3報)6および6'位トリチル置換セロビオースおよびメチルセロビオシドの完全アセチル化物の^<13>C-NMRスペクトル

概要

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The ^<13>C-NMR spectra of 6-and 6'-O-tritylcellobiose peracetates and methyl 6-and 6'-O-tritylcellobioside peracetates in chloroform-d were determined. ^<13>C signals were assigned by chemical shift comparisons with α- and β-D-glucopyranose pentaacetates, methyl β-D-glucopyranoside tetraacetate, methyl 6-O-trityl-β-D-glucopyranoside triacetate, methyl 4-O-methyl-β-D-glucopyranoside triacetate, methyl 4-O-methyl-6-O-trityl-β-D-glucopyranoside diacetate, and α-and β-cellobiose octaacetates. It was found that ^<13>C-NMR spectroscopy is a useful tool for determining which position of 6-or 6'-primary alcohol group is substituted with a trityl group. The effects of 6-and 6'-O-trityl substitutions upon the conformation around the interglycosidic linkage of the cellobiose are discussed by using the trityl substitution shifts in ^<13>C-NMR and by comparing the conformation of 6-O-trityl-α-cellobiose heptaacetate in the crystalline state obtained by an X-ray analysis.
公益社団法人日本薬学会の論文
1981-05-25