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BETA-RIBONUCLEOSIDES AND ALPHA-ARABINONUCLEOSIDES CONTAINING THE 1,2-BENZISOXAZOLE AND 1,2-BENZISOTHIAZOLE RINGS
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-beta-D-ribofuranose followed by basic deprotection gave the corresponding beta-D-ribonucleosides, and the silylated base of 1, when treated with 1-O-acetyl-2,3,5-tri-O-benzoyl-alpha-D-arabinofuranose in the presence of stannic chloride, afforded the corresponding alpha-arabinonucleoside. Structural proofs of these nucleosides are provided from elemental analyses and H-1 and C-13 nmr spectra.
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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics