Improved Yields in the Synthesis of Alkyl Glycosides
作者:
DonaldE. Koeltzow,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 1
页码: 125-128
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508062954
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Recent syntheses of alkyl glycosides have involved a rnodification of the Koenigs-Knorr reaction in which a sugar peracetate is first brominated and finally reacted with the desired alcohol in the presence of silver ion as a catalyst. In 1980 Rosevear et a1.2reported a simplified synthesis of alkyl glycosides in which the acetobromosugar was not isolated, but was reacted with the alcohol and the deacetylated final product was purified using column chromatography on Dowex 1. While yield s obtained for alkyl glucosides by this procedure were as high as 60%, those for alkyl maltosides were only 25%. More recently Landauer et a1.3 have reported yields of 55 to 68% in the preparation of alkyl malto-sides. However, their procedure involves t h e isolation and purification of the acetobromosugar intermediate and reported yields are calculated on the basis of this intermediate.
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