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DOI: 10.1055/s-2002-34216
Highly Efficient Discrimination of Fluorous Tags by β-Cyclodextrin Columns: New Isolation Method for Fluorous Mixture Synthesis
Publication History
Publication Date:
23 September 2002 (online)
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Abstract
High performance liquid chromatography (HPLC) packed with β-cyclodextrin columns eluted by reversed phase or fluorous phase shows excellent discrimination of fluorous tags. β-Cyclodextrin columns are superior to fluorous silica gel columns in view of efficient separation of compounds bearing short (CF3) to long (C9F19) tag.
Key words
β-cyclodextrin - chromatography - separation technique - combinatorial chemistry - fluorine chemistry
- 1
Nishikido J.Nanbo M.Yoshida A.Nakajima H.Matsumoto Y.Mikami K. Synlett 2002, 1613 - 2
Wilson LD.Verrall RE. J. Phys. Chem. B 1997, 101: 9270 -
3a
Curran DP.Furukawa T. Org. Lett. 2002, 4: 2233 -
3b
Zhang Q.Rivkin A.Curran DP. J. Am. Chem. Soc. 2002, 124: 5774 -
3c
Curran DP.Oderaotoshi Y. Tetrahedron 2001, 57: 5234 -
3d
Luo Z.Zhang Q.Oderaotoshi Y.Curran DP. Science 2001, 291: 1766 - 4
Curran DP. Synlett 2001, 1488 -
5a
Kamiusuki T.Monde T.Yano K.Yoko T.Konakahara T. Chromatographia 1999, 49: 649 -
5b
Konakahara T.Okada S.Monde T.Nakayama N.Furuhashi J.Sugaya J. Nihon Kagaku Kaishi 1991, 12: 1638 -
5c
Konakahara T,Nakayama N, andMonde T. inventors; Jpn. Pat. Dec. 2505267. - OD-H is packed with the cellulose 3,5-dimethylphenylcarbamate and helical structure is proposed for cellulose tris(phenylcarbamate). Review:
-
11a
Nakano T.Okamoto Y. Chem. Rev. 2001, 101: 4013 -
11b
Yashima E.Yamamoto C.Okamoto Y. Synlett 1998, 344 -
11c
Yashima E.Okamoto Y. Bull. Chem. Soc. Jpn. 1995, 68: 3289
References
SUMICHIRAL OA-7000 series are sold by Sumika Chemical Analysis Service. Catalog about SUMICHIRAL OA-7000 series: Welcome to SUMICHIRAL OA third edition. URL: http://www.scas.co.jp/.
7SUMICHIRAL OA-7000 is the column with unmodified β-CD bonded to the silica gel via saccharide (glucuroyl gluconoyl group) spacer; SUMICHIRAL OA-7100 is the column with unmodified β-CD bonded to the silica gel via alkyl group spacer; SUMICHIRAL OA-7500 is the column with β-CD, in which hydroxyl group is protected by methyl group, bonded to the silica gel via alkyl group spacer.
8Fluorinated sulfonamides (PhSO2NHCH2CnFn+1, n = 1, 3, 7) were also separated with OA-7000 or OA-7100 (mobile phase: gradient of MeOH/H2O).
9Retention time of esters 1a-c was as follows; 1a: 19.1 min, 1b: 28.6 min, 1c: 39.2 min.
10Retention time of sulfonates 2a-e with OA-7100 was as follows; 2a: 23.1 min, 2b: 16.9 min, 2c: 14.3 min, 2d: 10.8 min, 2e: 10.2 min.
12ZEORORA-H is 1,1,2,2,3,3,4-heptafluorocyclopentane and sold by ZEON CORPORATION. URL of ZEON CORPORATION: http://www.zeon.co.jp/.