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DOI: 10.1055/s-2004-831323
Rapid Oligosaccharide Synthesis on a Novel Benzyl-Type Fluorous Support
Publication History
Publication Date:
31 August 2004 (online)
Abstract
A novel benzyl-type fluorous support (HfBn-OH) has been easily prepared, and the HfBn group was successfully introduced to the anomeric position of the carbohydrate, then removed in high yield after working as a support. The use of the HfBn group made it possible to synthesize an oligosaccharide with minimal column chromatography purification. It was found that each HfBn derivative as a synthetic intermediate is easily purified only by fluorous-organic solvent extraction.
Key words
fluorous - oligosaccharide - support - rapid synthesis
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References
Compound 5: 1H NMR (CDCl3): δ = 1.73-1.95 (m, 8 H), 1.95-2.17 (m, 8 H), 2.39-2.82 (m, 16 H), 3.23-3.79 (m, 25 H), 4.68 and 4.70 (each s, 2 H, split of HO-CH 2 -Ph), 7.21-7.42 (m, 6 H). MALDI-TOF-MS: m/z calcd for C90H66F102N7O8 [M + H+]: 3310.3. Found: 3310.4.
9Compound 5 was obtained by treatment with sodium methoxide after coupling, because a slight excess amount of 4 further reacted with the hydroxyl function of 5 to give the undesired ester.
11The fluorocarbon solvent (EtOC4F9, NovecTM HFE-7200) is commercially available.
12The fluorocarbon solvent (FC-72, bp 76 °C, formally called FluorinertTM FC-72) is commercially available and consists of perfluorohexane isomers (C6F14).