Nucleosides and Nucleotides. 143. Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives.
- 1 January 1996
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 44 (2) , 288-295
- https://doi.org/10.1248/cpb.44.288
Abstract
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-N1-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.Keywords
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