Protecting Groups in Nucleosides and Nucleotides Synthesis. VIII. Synthesis of (4-Substituted 2-Picolyl 1-Oxide) halides and 2'-and 3'-O-(4-Substituted-2-picolyl 1-Oxide) nucleosides

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概要

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• A number of alkylating agents of the 4-substituted pyridine N-oxide series, such as (4-nitro-, 4-methylthio-, or 4-methoxy-2-picolyl 1-oxide) halide, have been prepared. Treatment of 2', 3'-O-(dibutylstannylene) uridine or 2', 3'-O-(dibutylstannylene) adenosine with the alkylating agents afforded the corresponding 2'-O- and 3'-O-(4-substituted 2-picolyl 1-oxide) nucleosides. 2'-O-(4-Nitro-2-picolyl 1-oxide) uridine was converted to the 4-methoxy-2-picolyl derivative on treatment with methanolic sodium methoxide at 60°. However, it was found that the treatment of adenosine with sodium hydride in DMF, followed by alkylation with (4-methoxy-2-picolyl 1-oxide) chloride gave a more satisfactory yield (56.4%) of 2'-O-(4-methoxy-2-picolyl 1-oxide) adenosine. 2'-O-(4-Methylthio-2-picolyl 1-oxide) adenosine could be similarly prepared in 36.7% yield. 4-Methoxy-2-picolyl protection was removable under milder conditions than 2-picolyl 1-oxide protection. Phosphorylation of 17 with phosphoryl chloride in triethyl phosphate gave the corresponding 5'-phosphate in 57.8% yield.

• 社団法人日本薬学会の論文
• 1980-10-25

著者

• 水野 義久

  School Of Pharmaceutical Sciences Kitasato University

• 水野 義久

  Faculty Of Pharmacy Kanazawa University

• 水野 義久

  北海道大学 薬

• 高橋 昭

  Faculty Of Pharmaceutical Sciences Tohoku University

• 遠藤 武

  Fuji Chemical Industry Co. Ltd.,

• 遠藤 武

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 稲城 安津子

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 遠藤 武

  Fuji Chemical Industry Co. Ltd.

• 稲城 安津子

  Faculty Of Pharmaceutical Sciences Hokkaido University

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