Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of Adenosine and Uridine Analogues Containing Conjugated Diene

공액 이중 결합을 갖는 Adenosine과 Uridine 유사체의 합성

  • Ro, Bong Oh (Chemistry Major, College of Education, Chosun University)
  • 노봉오 (조선대학교 사범대학 화학전공)
  • Published : 20010800
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Abstract

7'-Aldehyde-nucleosides analogue (2a, 2c) were synthesized from 6-N-benzoyl-2',3'-O-isopropylideneadenosine and uridine. The condensation of 2 with ethoxycarbonylmethylene Wittig reagent produced the adenosine and uridine analogues containing extended conjugated diene and ethoxycarbonyl group, ethyl-1',5',6',7',8'-pentadeoxy-1'-(adenin-9-yl)-$\beta$-D-ribo-nona-5'(E),7'(E)-dienofuranuronate (4b) and ethyl-1'. 5',6',7',8'-pentadeoxy-1'-(uracil-1-yl)-$\beta$-D-ribo-nona-5'(E),7'-(E)-dienofuranuronate (4c). 9-[8',8'-dibromo-5',6',7',8' -tetradeoxy-$\beta$-D-ribo-octa-5'(E),7'(E)-diene]nucleosides (6b, 6c) were also prepared from 2 with similar method.

7'-Aldehyde-nucleoside 유사체(2a, 2c)을 6-N-benzoyl-2',3'-O-isopropylideneadenosiner과 uridine으로부터 합성하였다. 2와 Wittig reagent인 ethoxycarbonylmethylene을 축합시켜 ethoxycarbonyl group을 갖는 탄소수를 증가시킨 공액 이중 결합을 지닌 nucleosi de 유사체, ethyl-1',5',6',7',8'-pentadeoxy-1'-(adenin-9-yl)-$\beta$-D-ribo-nnona-5'(E).7'(E)-dienofuranuronate(4b), ethyl-1',5',6',7',8'-pentadeoxy-1'-(uracyl-1-yl)-$\beta$-D-ribo-nona-5'(E),7'(E)-dienofuranuronate(4c)을 얻었다. 또한 2와 CBr4, Ph3P을 반응시켜 공액 이중 결합을 지닌 9-[8',8'-dibromo-5',6',7',8'-tetradeoxy-$\beta$-D-ribo-octa-5'(E),7'(E)-diene]nucleosides (6b,6c) 유사체를 각각 합성하였다.

Keywords

References

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