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有机化学
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有机化学 ›› 2001, Vol. 21 ›› Issue (3): 205-210. 上一篇    下一篇

研究论文

(3'→ 5')亚甲基缩醛连接的二聚和三聚体脱氧核苷的另法 合成

余建鑫;张万年;李科;周有骏;朱驹;吕加国   

  1. 第二军医大学药学院.上海
  • 发布日期:2001-03-25

An alternative route to (3' → 5') methylene acetal linked di-and trideoxynucleosides

Yu Jianxin;Zhang Wannian;Li Ke;Zhou Youjun;Zhu Ju;Lu Jiaguo   

  1. Univ of No.2 Military Medicine, College of Pharmacy.Shanghai
  • Published:2001-03-25

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376

被引次数

5

3'-O-(甲硫甲基)缩醛的脱氧核苷(1)与N-碘代丁二酰亚胺(NIS)和二苯基次膦酸反应得到相应的3'-O-(二苯膦酰氧)甲基缩醛(2)。在三甲基硅三氟甲磺酸酯(TMSOTf)的条件下，后者与3'-位保护的脱氧核苷(5)缩合，得到(3'→5')甲缩醛连接的二聚体d[(B1-m-B2)](m=次甲基)(6)。同样的，2(B=T或B=C)与3'-位保护的二聚体9(T-m-T或C-m-T)缩合，可得到相应的三聚体10(T-m-T-m-T,C-m-T-m-T和T-m-C-m-T)。

关键词: 甲缩醛, 二聚体, 核苷, 三聚物, 脱氧核苷, 合成法, 寡核苷酸

Reaction of deoxynucleosides 3'-O-(methylthiomethyl)acetal (1) with N-iodosuccinimide (NIS) and diphenylphosphinic acid furnished the corresponding 3'-O-(diphenylphosphinyloxy)methyl acetal (2). Condensation of the altter with 3'-protected deoxynucleoside (5) in the presence of trimethylsilyl trifluomethanesulfonate (TMSOTf) afforded the (3'→ 5') methylene acetal linked d(B1-m-B2) dimers (6). In addition, the coupling of donor 2 (B=T or C) with 3'-protected dimer 9 (T-m-T or C-m-T) yielded corresponding trimers 10 (T-m-T-m-T, C-m-T-m-T and T-m-C-m-T).

Key words: FORMALDEHYDE ACETAL, DIMER, NUCLEOSIDE, TRIMER, DEOXYRIBONUCLEOSIDE, SYNTHESIS METHODS, OLIGONUCLEOTIDE

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