Synthesis of 2'-Substituted Derivatives of Neplanocin A (Nucleosides and Nucleotides. XLIV)
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概要
- 論文の詳細を見る
Neplanocin A (1) and N^6-benzoylneplanocin A (2) were converted to the corresponding 3', 6'-O-(tetraisopropyldisiloxane-1,3-diyl)-neplanocin A's (3,4). The 2'-hydroxy group in 3 and 4 was triflated (5,6). Nucleophilic displacement of 5 and 6 with a number of nucleophiles (I^-, Br^-, Cl^-, N_3^-, AcO^-, AcS^-) in hexamethylphosphoric triamide afforded the corresponding 2' (R)-substituted derivatives in high yields. The 2' (S)-azido derivatives were obtained in a similar manner from arabinoneplanocin A prepared by this method. Adenosine was also converted to 2' (R)-substituted derivatives, including arabinofuranosyladenine, as well as 2' (S)-substituted adenosines. The physical properties of these 2'-substituted derivatives of neplanocin A and adenosine, including nuclear magnetic resonance and circular dichroism spectra, are presented.
- 公益社団法人日本薬学会の論文
- 1983-05-25
著者
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上田 亨
Faculty of Pharmaceutical Science, Hokkaido University
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上田 亨
Faculty Of Pharmaceutical Sciences 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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