Application of Sugar Phosphonates for the Preparation of Higher Carbon Monosaccharides
作者:
Slawomir Jarosz,
Stanislaw Skóra,
Artur Stefanowicz,
Mateusz Mach,
Jadwiga Frelek,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1999)
卷期:
Volume 18,
issue 8
页码: 961-974
ISSN:0732-8303
年代: 1999
DOI:10.1080/07328309908544046
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Reaction of sugar derived phosphonates [Sug-C(O)CH2P(O)(OMe)2] with sugar aldehydes (Sug'-CHO) provides the higher enones of the general formula Sug-C(O)CH=CH-Sug' with thetransconfiguration of the double bond. The phosphonate method is superior to the previously used phosphorane methodology [Sug-C(O)CH=PPh3+ Sug'-CHO] since sugar phosphonates can be prepared in much higher yields and are much more nucleophilic than corresponding phosphoranes. The sugar enones are reduced to appropriate allylic alcohols with zinc borohydride; the stereoselectivity of this process is >97:3 (with the D-glyceroisomer predominating) when the carbonyl group is placed at the α-position to the sugar ring. CD spectroscopy was used for the determination of the configuration of higher sugar allylic alcohols.
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