Synthesis of 2'(R)-Substituted Neplanocin A's (Nucleosides and Nucleotides. XXXVII)
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概要
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Neplanocin A (I) was treated with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane to give 3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl) neplanocin A (II), which was converted to the 2'-O-trifluoromethanesulfonyl derivative (III). Nucleophilic substitution of III with a number of nucleophiles (AcO^-, AcS^-, N_3^-, Cl^-, Br^-, I^-) in hexamethylphosphoric triamide afforded the respective 2' (R)-substituted derivatives in high yield. The halogenated derivatives were reduced with tri-n-butyltin hydride to the 2'-deoxy compound. 2'-O-Thiocarbonylimidazoyl-3', 5'-O-(tetraisopropyldisiloxane-1,3-diyl) neplanocin A was also reduced to the 2'-deoxy derivative. The deprotection of the bifunctional silyl group with tetra-n-butylammonium fluoride afforded 2' (R)-AcO, -AcS, -N_3,-Cl, -Br, -I, and 2'-deoxy neplanocin A's, respectively. Physical data of these compounds including nuclear magnetic resonance, mass spectrum, and circular dichroism were given.
- 公益社団法人日本薬学会の論文
- 1981-02-25
著者
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上田 亨
Faculty of Pharmaceutical Science, Hokkaido University
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平野 孝夫
Research Laboratories, Toyo Jozo Co., Ltd.,
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福川 清史
Reseach Laboratories Toyo Jozo Co. Ltd.
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上田 亨
北海道大学薬学部
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福川 清史
Faculty of Pharmaceutical Sciences, Hokkaido University
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平野 孝夫
Research Laboratories Toyo Jozo Co. Ltd.
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