β-Cyclodextrin Columns for Separation of Fluorous and Non-Fluorous Compounds: How To Use β-Cyclodextrin Columns in Fluorous Mixture Synthesis and Racemic Synthesis

Koichi Mikami; Hiroshi Matsuzawa; Seiji Tekeuchi; Yutaka Nakamura; Dennis P. Curran

doi:10.1055/s-2004-835649

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Synlett 2004(15): 2713-2716
DOI: 10.1055/s-2004-835649

LETTER

β-Cyclodextrin Columns for Separation of Fluorous and Non-Fluorous Compounds: How To Use β-Cyclodextrin Columns in Fluorous Mixture Synthesis and Racemic Synthesis

Koichi Mikami*^a, Hiroshi Matsuzawa^a, Seiji Tekeuchi*^b, Yutaka Nakamura^b, Dennis P. Curran^c
^a Department of Applied Chemistry, Tokyo Institute of Technology, Meguro-ku, Tokyo, 152-8552, Japan
Fax: +81(3)57342776; e-Mail: kmikami@o.cc.titech.ac.jp;
^b Niigata University of Pharmacy and Applied Life Sciences, Niitsu, 956-8603, Japan
^c Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA

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Publication History

Received 26 August 2004
Publication Date:
12 November 2004 (online)

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Abstract

Guidelines for the use of β-cyclodextrin columns in fluorous and non-fluorous mixture synthesis, and racemic synthesis are suggested. Fluorous compounds can be separated more efficiently with SUMICHIRAL OA-7000 and -7100, while non-fluorous compounds can be separated better with SUMICHIRAL OA-7500. When the ratio of water in the mobile phase is large (>20%), the guard column (GL cart) can improve the separability of the fluorinated mixture.

Key words

β-cyclodextrin - chromatography - combinatorial chemistry - fluorous mixture synthesis - racemic synthesis

References

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7

GL cart is commercially available from GL Sciences. URL of GL Sciences: http://www.gls.co.jp/

10

Mismatched compounds with fluorous or non-fluorous tags are now under investigation with OA-7000 and -7100, in particular.