The Journal of Natural Sciences (자연과학논문집)
- Volume 9 Issue 1
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- Pages.95-104
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- 1997
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- 1225-6196(pISSN)
Synthesis of Pyrimidine Nucleosides as a Potential Asymmetric Catalysts
핵산유도체의 비대칭촉매 가능성연구
- Youn, In-Kwon (Department of Chemistry, Pai Chai University) ;
- Beak, Gi-Hueon (Department of Chemistry, Pai Chai University)
- Published : 1997.02.28
Abstract
We synthesized the following series of 3', 5'hydroxy modified thymidine analogs to check the potential asymmetric catalytic effects. 3'-monomethylammino and dimethylaminothymidine was synthesized from thymidine via 8 step and 7 step in 38%, 20% overall yields respectively. 5'Acetyl-3'-dimethylamino thymidine was prepared from thymidine via 8 step in 40% overall yield. 5‘-TBS-3'-up-t BOC methylamino thymidine was prepared from thymidine via 6 step in 30% overall yield. 3'-acetyl-5'-t BOC amino thymidine was prepared from thymidine via 7 step in 31% overall yield.
본 연구에서는 thymidine으로부터 시작하여 3'-OH과 5'-OH의 각각의 변형, 동시의 변형을 통해 크게 5종의 amino thymidine 골격의 촉매를 합성하였다. 다양한 thymidine 화합물들이 새로운 키랄 보조체로서의 촉매효과를 위해 우선 3'-OH 자리에 mono-methylamino thymidine과 dimethylamino thymidine을 합성하고, 이들의 합성과정을 응용하여 5'-OH을 Ac-O로 변환한 5'-acetyl-3'-dimethylamino thymidine과 5'-OH를 TBS로 변환하고 up위치의 azido화합물인 5'-TBS-3'-Up-tBOC methylamino thymidine을 합성하였다. 그리고, 5'-OH를 amino group으로 변환하고 3'-OH를 -Me로 변환한 화합물 3'-acetyl-5'-tBOC-amino thymidine을 합성하였다.