β-Ribo- and α-arabinonucleosides containing the 1,2-benzisoxazole and 1,2-benzisothiazole rings |
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Authors: | Kiyotaka Yoshii Yoshihiro Ohba Tarozaemon Nishiwaki |
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Abstract: | The reaction of the silylated base of 1,2-benzisoxazol-3(2H)-one ( 1 ) and its 7-methyl derivative 5 and 5-methyl-1,2-benzisothiazol-3(2H)-one ( 9 ), respectively, with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose followed by basic deprotection gave the corresponding β-D-ribonucleosides, and the silylated base of 1 , when treated with 1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-arabinofuranose in the presence of stannic chloride, afforded the corresponding α-arabinonucleoside. Structural proofs of these nucleosides are provided from elemental analyses and 1H and 13C nmr spectra. |
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