14 配糖体の^<13>C-NMRの研究 : 選択的重水素化の応用
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Recently, Stuart et al. reported that hexopyranosides and their derivatives were readily deuterated at carbon atoms bound to free OH by hot D_2O containing deuterated Raney nickel. For the purpose to the application of this procedure to ^<13>C-NMR spectroscopy of natural glycosides, the further examination of the condition of this reaction and partial epimerization of arabinoside, xyloside and rhamnoside with Raney nickel have been investigated. On prolonged treatment with Raney nickel in D_2O, methyl α-L-arabinopyranoside(2) yielded methyl β-D-xylopyranoside(3) and methyl α-L-lyxopyranoside(5) and 3 gave 2 and β-D-ribopyranoside(6), while methyl α-L-rhamnopyranoside(4) was epimerized slowly rather than 2 and 3, affording methyl 6-deoxy α-L-glucopyranoside(7). Selection of the type of Raney nickel, reaction time and solvents as well as comparison of the rate of C-deuteration of each carbinyl carbon of 2, 3, 4 and methyl β-D-glucopyranoside(8) with deuterated Raney nickel were also studied. By means of this procedure, the previous assignments of the carbon signals of α-1,6-glucan(10)(C-4,-5) and methyl β-cellobio-side(11)(C-3,-5) were revised as shown in the chart. Further, confirmation of the assignments of the carbon signals of β-sophorosyl moiety of ginsenosides-Rf(16) and -Rb_1(12) by this procedure led to the elucidation of the structures of the sugar moieties of new saponins, notoginsenosides-R1(13) and -R2(14)(isolated from San-chi Ginseng) and majonosides-R1(17) and -R2(18)(obtained from rhizomes of Panax japonicus var. major).
- 天然有機化合物討論会の論文
- 1981-09-10
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