Synthesis of 3-Aryl-5-C-Glycosylisoxazoles from Several Aldehydo-Sugar Derivatives
作者:
J. M. Sanz Báñez,
J. A. Sastre López,
M. R. Molina Patiño,
T. Gómez Santacana,
C. Romero-Ávila García,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1999)
卷期:
Volume 18,
issue 4
页码: 403-417
ISSN:0732-8303
年代: 1999
DOI:10.1080/07328309908544005
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
The synthesis of several 3-aryl-5-glycosylisoxazole derivatives has been achieved. By condensation of the protected aldehydo-sugars 2,3-O-isopropylidene-D-glyceraldehyde (1), 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (2) and D-xylose (3), and 2,5-anhydro-3,4,5-tri-O-benzoyl-D-mannose (4) with benzoylmethylenetriphenylphosphorane, enulose derivatives were formed, which were later converted into a,ß-unsaturated ketoximes. These ketoximes were oxidatively cyclized with iodine and, after removal of the hydroxyl protecting groups, 3-phenyl-5-glycosylisoxazoles were formed.
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