Purines. XI. The Synthesis of N-Alkoxyadenosines and Their 2', 3'-O-Isopropylidene Derivatives
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概要
- 論文の詳細を見る
Alkylation of adenosine 1-oxide (I) and its 2', 3'-O-isopropylidene derivative (V) with alkyl halides in N, N-dimethylacetamide furnished the corresponding 1-alkoxy derivatives (IIa-f). The free bases, obtained from IIa-f, readily underwent rearrangement to give the isomeric N^6-alkoxy derivatives (IVa-f) when heated in water. Treatment of 1-benzyloxyadenosine perchlorate (IIc : X=ClO_4) with water at pH 9.5 and 39-41°for 4 hr afforded the ring-opened intermediate (IIIc)(79% yield), which was recyclized in hot water (pH 7) to IVc. In alternative synthesis of IVa, b, c, condensation of 6-chloro-6-β-D-ribofuranosylpurine (VIa) with the appropriate alkoxyamines proceeded smoothly. Removal of the isopropylidene group from IVe under acid conditions or exchange amination of adenosine with ethoxyamine at pH 5 also yielded N-ethoxyadenosine (IVb).
- 公益社団法人日本薬学会の論文
- 1973-08-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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茂籠 哲
Faculty Of Pharmaceutical Sciences Kanazawa University
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呉 欽敬
Faculty Of Pharmaceutical Sciences University Of Tokyo
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