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Synthesis of Fluorinated Carbohydrates

 

作者: PeterJ. Card,  

 

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

页码: 451-487

 

ISSN:0732-8303

 

年代: 1985

 

DOI:10.1080/07328308508082671

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

The similarities in bond length and polarization between C-F and C-OH, as well as the altered hydrogen-bonding properties present in carbohydrates bearing a fluorine atom in place of an hydroxyl group can be exploited in place of an hydroxyl group can be exploited in biochemical investigations (enzyme-carbohydrate interactions, Lectin-carbohydrate affinities, antiobody-carbohydrate binding, etc.).1–5In addition, the different chemistries exhibited by the flourinated carbohydrates have made them important reagents in both metabolic studies and disease diagnosis such as the use of 2-deoxy-2-[18f]-D-fluoroglucose in positron emission tomography. 6,7 Becasue of their widespread utlity, the synthesis of fluorinated carbohydrates is of importance. However, the Introduction of fluorine into a carbohydrate moiety can be an arduous task because of (1) the protection and deprotection steps required to set up the desired hydroxyl group for the introduction of fluoride, (2) the low nucleophilicity fo fluoride ion, and (3) fluoride ion catalyzed elimination reactions. 8,9 The search for Milder and more selective methods for the introduction of fluorine into Carbohydrates has continued at a rapid pace and it is appropriate to review som of the recent results.

 

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