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Synthesis 2009(7): 1224-1226
DOI: 10.1055/s-0028-1088010
DOI: 10.1055/s-0028-1088010
PSP
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Regioisomerically Pure 5-Functionalized 2′,7′-Dichlorofluoresceins
Further Information
Received
12 November 2008
Publication Date:
06 March 2009 (online)
Publication History
Publication Date:
06 March 2009 (online)
Abstract
Regioisomerically pure 2′,7′-dichloro-5-nitrofluorescein was isolated on a multigram scale, and used as an intermediate for the generation of three compounds that might be used for labeling biomolecules, namely the corresponding amino, azido, and (4,6-dichloro-1,3,5-triazin-2-ylamino) derivatives.
Key words
fluorescence - chromophores - condensation - heterocycles - regioselectivity
- 1
Walkup GK.Burdette SC.Lippard SJ.Tsien RY. J. Am. Chem. Soc. 2000, 122: 5644 -
2a
Lyttle MH.Carter TG.Cook RM. Org. Process Res. Dev. 2001, 5: 45 -
2b
Sun W.-C.Gee KR.Klaubert DH.Haugland RP. J. Org. Chem. 1997, 62: 6469 -
2c
Jiao G.-S.Han JW.Burgess K. J. Org. Chem. 2003, 68: 8264 -
2d
Ueno Y.Jiao G.-S.Burgess K. Synthesis 2004, 2591 -
3a
Haugland RP,Naleway JJ, andZhang YZ. inventors; US 5208148. -
3b
Nagano T,Kikuchi K, andHirano T. inventors; WO 0162755. - 4
Coons AH.Kaplan MH. J. Exp. Med. 1950, 91: 1 -
5a
Tornoe CW.Christensen C.Meldal M. J. Org. Chem. 2002, 67: 3057 -
5b
Rostovtsev VV.Green LG.Fokin VV.Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596 - 6
Gustafson GR.Baldino CM.O’Donnell MME.Sheldon A.Tarsa RJ.Verni CJ.Coffen DL. Tetrahedron 1998, 54: 4051 - 7
Blakeslee D. J. Immunol. Methods 1977, 17: 361 -
8a
Pattarawarapan M.Reyes S.Xia Z.Zaccaro MC.Saragovi HU.Burgess K. J. Med. Chem. 2003, 46: 3565 -
8b
Angell Y.Chen D.Brahimi F.Saragovi HU.Burgess K. J. Am. Chem. Soc. 2008, 130: 556