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β‐Ribo‐ and α‐arabinonucleosides containing the 1,2‐benzisoxazole and 1,2‐benzisothiazole rings
Author(s) -
Yoshii Kiyotaka,
Ohba Yoshihiro,
Nishiwaki Tarozaemon
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300125
Subject(s) - chemistry , benzoyl chloride , base (topology) , derivative (finance) , chloride , medicinal chemistry , nmr spectra database , stereochemistry , organic chemistry , spectral line , mathematical analysis , physics , mathematics , astronomy , financial economics , economics
Abstract The reaction of the silylated base of 1,2‐benzisoxazol‐3(2 H )‐one ( 1 ) and its 7‐methyl derivative 5 and 5‐methyl‐1,2‐benzisothiazol‐3(2 H )‐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 1 H and 13 C nmr spectra.