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化学学报
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化学学报 ›› 1988, Vol. 46 ›› Issue (12): 1195-1200. 上一篇    下一篇

研究论文

核糖核苷酸和核糖核苷的N-羧酰咪唑选样性酰化

汪猷;徐耀忠;杨再完;刘象元;王绮文   

  1. 中国科学院上海有机化学研究所
  • 发布日期:1988-12-15

Selective acylation of ribonucleotides and ribonucleosides with N-acylimidazole

WANG YOU;XU YAOZHONG;YANG ZAIWAN;LIU XIANGYUAN;WANG QIWEN   

  • Published:1988-12-15

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540

被引次数

1

应用N-羧酰咪唑在合适的条件下可按制备性规模进行选择性地酰化核糖核苷酸和核糖核苷, 得率为50-80%. 对反应机制作了初步探讨.

关键词: 咪唑 P, 羧酸, 反应机理, 选择性, 吗啉 P, 空间效应, 酰化, 核糖核苷, 核糖核苷酸

Selective acylation of ribonucleotides and ribonucleosides can be achieved by using N-acylimidazole on a preparative scale with good yields (50-80%). For uridine-3'-phosphate (Up): in the presence of 4-morpholino-N,N'-dicyclohexylcarboxamidine (I) the 2'-O-acyl-deriv. was the main product, while in the presence of an excess of tetraethylammonium hydroxide (II) the 5'-O-acyl-deriv. was the main product. For ribonucleosides (UR or AR or yR): in the presence of I, the acylation took place preferably on 2'-OH or 3'-OH of ribonucleoside and only 3'-O-acyl-derivs. can be isolated by crystallization; in the presence of an excess of II 5'-O-acyl-deriv. was obtained as the main product. Arabonuleoside and deoxyribonucleoside were only slowly acylated to form 5'-O-acyl-derivs. as the main products by acylimidazole in the presence of I. Possible mechanisms of acylation were discussed.

Key words: IMIDAZOLE P, CARBOXYLIC ACID, REACTION MECHANISM, SELECTIVITY, MORPHOLINE P, STERIC EFFECT, ACYLATION, RIBONUCLEOSIDE, RIBONUCLEOTIDE

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