Rapid Oligosaccharide Synthesis Using a Fluorous Protective Group

The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography pu...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-08, Vol.69 (16), p.5348-5353
Main Authors: Miura, Tsuyoshi, Goto, Kohtaro, Waragai, Hideki, Matsumoto, Hiroharu, Hirose, Yuriko, Ohmae, Masashi, Ishida, Hide-ki, Satoh, Ai, Inazu, Toshiyuki
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Chromatography, Thin Layer
Exact sciences and technology
Fluorine - chemistry
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Structure
Oligosaccharides - chemical synthesis
Organic chemistry
Preparations and properties
Protective Agents - chemistry
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Summary:The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous−organic solvent extraction and monitored by TLC, NMR, and MS.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049425k