The Preparation ofO-Trifluoromethyl Carbohydrates
作者:
GeorgeL. Trainor,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 4
页码: 545-563
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508082676
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
A simple method for the preparation ofO-tri-fluoromethyl carbohydrate derivatives is reported. Carbohydrate derivatives bearing excellent leaving groups can react with tris(dimethylamino)sulfonium trifluoromethoxide (TAS+CF3-O-) to afford trifluoro-methoxy-substituted compounds along with varying amounts of the corresponding deoxyfluoro products. Primary and secondary triflates afford the corresponding trifluoromethyl ethers. Displacement at a secondary center occurs with complete inversion of configuration. Glucosyl bromides react to form mixtures of trifluoromethyl glucosides and glucosyl fluorides.
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