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Preparation and Structure of (E)-1-(3′-Hydroxy-2-Furanyl)-3-(3″-Hydroxy-4″-Methoxyphenyl)-2-Propen-1-One

 

作者: JamesC. Goodwin,   Larry Tjarks,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1988)
卷期: Volume 7, issue 1  

页码: 133-140

 

ISSN:0732-8303

 

年代: 1988

 

DOI:10.1080/07328308808058908

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

A facile procedure is presented for the synthesis of (E)-1-(3′-hydroxy-2′-furanyl)-3-(3″-hydroxy-4″-methoxyphenyl)-2- propen-1-one (6). Galactosylisomaltol (1) was condensed with isovanillin (2) under strong alkaline conditions at 25 [ddot]C to form (E)-1-(3′-O-β-D-galactopyranosyloxy-2′-furanyl)-3-(3″- hydroxy-4″-methoxyphenyl)-2-propen-1-one (4). (E)-1-(3′-hydroxy-2′-furanyl)-3-(3″-hydroxy-4″-methoxyphenyl)-2-propen-1-one (6) was obtained by acid hydrolysis of 4 in a 53.9% yield. This hetero-cyclic 2-propen-1-one was characterized on the basis of spectral data (IR and1H NMR), physicochemical properties, and conversion to a mono-O-acetyl derivative.

 

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