Chin. J. Org. Chem. ›› 2001, Vol. 21 ›› Issue (3): 205-210. Previous Articles     Next Articles

(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

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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