Chemical and Pharmaceutical Bulletin p. 288 - 295 (1996)
Update date:2022-07-29
Topics:
Minakawa
Sasabuchi
Kiyosue
Kojima
Matsuda
An efficient and large scale chemical synthesis of 5-aminoimidazole-4- carboxamide (AICA) 2'-deoxyriboside (5a) and its 3'-deoxyriboside 5b is described. Treatment of 3',5'-di-O-acetyl-N1-triphenylmethyl-2'-deoxyinosine (3a) with 5N 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.
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