化学学报 ›› 1990, Vol. 48 ›› Issue (9): 927-930. 上一篇    下一篇

研究论文

碳苷研究 XXIII. 三-O-乙酰基葡萄糖和半乳糖碳苷的合成及结构的测定

邱东旭;乔梁;岳保珍;蔡孟深   

  1. 北京医科大学药学院
  • 发布日期:1990-09-15

Studies on C-glycosides XXIII. Synthesis and assignment of the configuration of Tri-O-acetyl-C-aryl-D-gluco-and galacto-pyranosides

QIU DONGXU;QIAO LIANG;YUE BAOZHEN;CAI MENGSHEN   

  • Published:1990-09-15

本文报道了葡萄糖和半乳糖碳苷的选择性乙酰化。通过比较四-O-乙酰基和三-O-乙酰基碳苷的^1H NMR谱证明糖环的2位羟基没有发生乙酰化。三-O-乙酰基半乳糖碳苷的构型用^1^3C NMR进行了鉴定。由其^1H NMR谱与通常规律相反的原因, 讨论了乙酰化的机理。

关键词: 反应机理, 碳13核磁共振谱法, 葡萄糖, 质子磁共振谱法, 糖苷, 半乳糖, 结构分析, 乙酰化, 乙酰基

Selective acetylation of aryl D-gluco- and galactopyranosides was reported. By comparing 1H NMR spectra of tri- and tetra-O-acetyl-C-aryl-D-glucopyranosides, it was shown that the hydroxy group at 2'-C position was not acetylated in the triacetate. In addition, when H NMR spectra were used to assign the configuration of tri-O-acetyl-b-C-aryl-D-galactopyranosides, the results did not follow the common rule. But 13C NMR spectra could give the correct results. A possible mechanism was proposed.

Key words: REACTION MECHANISM, C13 NMR SPECTROMETRY, GLUCOSE, PROTON MAGNETIC RESONANCE SPECTROMETRY, GLYCOSIDE, GALACTOSE, STRUCTURAL ANALYSIS, ACETYLATION, ACETYL GROUP

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