Nucleosides and nucleotides. 143. Synthesis of 5-amino-4- imidazolecarboxamide (AICA) deoxyribosides from deoxyinosines and their conversion into 3-deazapurine derivatives

Article abstract of DOI:10.1248/cpb.44.288

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.

Full text of DOI:10.1248/cpb.44.288

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service

NII-Electronic Library Service