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Synthesis and Characterization of the Naturally Occurring Monocyclic γ-Pyrone Glucosides

 

作者: JamesH. Looker,   MichaelS. Fisher,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1985)
卷期: Volume 4, issue 3  

页码: 381-392

 

ISSN:0732-8303

 

年代: 1985

 

DOI:10.1080/07328308508070188

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

β-D-Glucosides of pyromeconic acid (3-hydroxy-4-oxo-4H-pyran), maltol (3-hydroxy-2-methyl-4-oxo-4H-pyran) and α-hydroxymaltol (3-hydroxy-2-hydroxymethyl-4-oxo-4H-pyran) were synthesized in one pot by reaction of stoichiometric amounts of acetobromoglucose and preformed hydroxypyrone anion followed by catalytic deacetylation with methanolic KOH. Products were identified and characterized by comparison of mp and molar rotation with literature, and by FAB-MS, negative ferric chloride test, and H-1 and C-13 NMR. All glycosides were levorotatory,betaand gave recognizable pseudo-molecular ions.

 

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