Nucleosides and Nucleotides. 143.Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives
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概要
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An efficient and large scale chamical synthesis of 5-aminoimidazole-4-carboxamide (AICA) 2'-deoxyriboside (5a) and its 3'-deoxyriboside 5b is described. Treatment of 3', 5'-di-O-acetyl-N^1-triphenylmethyl-2'-deoxyinosine (3a) with 5 N NaOH in EtOH, followed by anhydrous trifluoroacetic acid gave 5a in 59% yield from 2'-deoxyinosine (1a). AICA 3'-deoxyriboside (5b) was also obtained in a similar manner as for 5a in 73% yield from 3'-deoxyinosine (1b). Conversion of these AICA derivatives (5a, b) into 3-deazapurine derivatives (9a, b, 15a, b, 20a, b) is also described.
- 公益社団法人日本薬学会の論文
- 1996-02-15
著者
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Minakawa Noriaki
Faculty Of Pharmaceutical Sciences Hokkaido University
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Kiyosue Arihiro
Faculty Of Pharmaceutical Sciences Hokkaido University
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Matsuda Akira
Faculty Of Pharmaceutical Sciences Hokkaido University
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SASABUCHI Yoshimasa
Faculty of Pharmaceutical Sciences, Hokkaido University
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KOJIMA Naoshi
Faculty of Pharmaceutical Sciences, Hokkaido University
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Kojima Naoshi
Faculty Of Pharmaceutical Sciences Hokkaido University
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Sasabuchi Yoshimasa
Faculty Of Pharmaceutical Sciences Hokkaido University
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- Nucleosides and Nucleotides. 143.Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives