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Paper | Regular issue | Vol 36, No. 7, 1993, pp.1617-1623
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6370
C-Nucleosides. 21. Synthesis of Isoxazole C-Nucleoside from Furanone Glycoside via Enaminone Glycoside

Isamu Maeba,* Yasutaka Ito, Masakazu Wakimura, and Chihiro Ito

*Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, Japan

Abstract

Synthesis of the versatile and stable C-nucleoside precursor enaminone glycosides (3a,b) was achieved by reaction of furanone glycoside (1) with 2- and 4-aminophenols. Treatment of enaminone (3b) with hydroxylamine hydrochloride yielded 5-hydroxy-4,5-dihydroisoxazole (5), which on dehydration with toluene-p-sulfonic acid in benzene gave 5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)isoxazole (6). Deblocking of compound (6) with sodium carbonate gave 5-(β-D-ribofuranosyl)isoxazole (7).