RSS-Feed abonnieren
DOI: 10.1055/s-0031-1289685
A Cost-Effective, Column-Free Route to Ethylene Glycol Oligomers EG6, EG10, and EG12
Publikationsverlauf
Publikationsdatum:
03. Februar 2012 (online)
Abstract
Although monodisperse ethylene glycol (EG) oligomers are important in a wide range of applications (ranging from drug therapeutics to materials science and engineering), their cost - especially for longer EG oligomers is often prohibitive. For example, decaethylene, EG10, and dodecaethylene, EG12, glycols cost hundreds of dollars per gram, and are only available from most vendors, including Sigma-Aldrich, in the polydispersed form. This high-cost is, in large part, due to laborious nature of synthesis and, above all, purification steps involved. Therefore, the motivation of our work was to design a cost-effective route to the EG oligomers that would altogether avoid the column-chromatography purification. This was achieved by a simple synthetic strategy, which combines bidirectional growth of the EG chains with the protection scheme using easy-to-remove trityl groups.
Key words
ethylene glycol oligomer - monodisperse - column-free - EG oligomer - PEGs - cost-effective
- Supporting Information for this article is available online:
- Supporting Information
- 1
Haag R.Kratz F. Angew. Chem. Int. Ed. 2006, 45: 1198 - 2
Pirawattana T.Srinophakun T. Int. J. Mol. Sci. 2008, 9: 2290 - 3
Palma JAD.Cleveland MV.McGowan J.Herrera JL. Am. J. Gastroenterol. 2007, 102: 1964 - 4
Krause TL.Bittner GD. Proc. Natl. Acad. Sci. U.S.A. 1990, 87: 1471 - 5
Corpet DE.Parnaud G.Delverdier M. Cancer Res. 2000, 60: 3160 - 6
Rubio-Garcia J.Coppel Y.Lecante P.Mingotaud C.Chaudret B.Gauffre F.Kahn ML. Chem. Commun. 2011, 47: 988 - 7
Ahmed SA.Tanaka M. J. Org. Chem. 2006, 71: 9884 - 8
Andrus MB.Turner TM.Updegraff EP.Sauna ZE.Ambudkar SV. Tetrahedron Lett. 2001, 42: 3819 - 9
Bartsch RA.Cason CV.Czech BP. J. Org. Chem. 1989, 54: 857 - 10
Burkett BA.Chan TH. Synthesis 2004, 1007 - 11
Wilken J.Kent SBH. Curr. Opin. Biotechnol. 1998, 9: 412 - 12
Knuf EC.Jiang J.-K.Gin MS. J. Org. Chem. 2003, 68: 9166 - 13
Kochendoerfer GG. Curr. Opin. Chem. Biol. 2005, 9: 555 - 14
Loiseau FA.Hii KKM.Hill AM. J. Org. Chem. 2004, 69: 639 - 15
Lumpi D.Braunshier C.Hametner C.Horkel E.Zachhuber B.Lendl B.Fröhlich J. Tetrahedron Lett. 2009, 50: 6469 - 16
Pilkington-Miksa MA.Sarkar S.Writer MJ.Barker SE.Shamlou PA.Hart SL.Hailes HC.Tabor AB. Eur. J. Org. Chem. 2008, 2900 - 17
Witt D.Klajn R.Barski P.Grzybowski BA. Curr. Org. Chem. 2004, 8: 1763 - 18
Pedrosa N.Pàmies JC.Coutinho JAP.Marrucho IM.Vega LF. Ind. Eng. Chem. Res. 2005, 44: 7027 - 19
Pant HR.Bajgai MP.Nam KT.Chu KH.Park S.-J.Kim HY. Mater. Lett. 2010, 64: 2087 - 20
Takahashi H.Kyu T.Trans-Cong Q.Yano O.Soen T. J. Polym. Sci., Part B: Poly. Phys. 1991, 29: 1419 - 21
Zalipsky S. Adv. Drug Deliv. Rev. 1995, 16: 157 - 22
Brocchini S.Godwin A.Balan S.Choi J.-w.Zloh M.Shaunak S. Adv. Drug Deliv. Rev. 2008, 60: 3 - 23
Abuchowski A.van Es T.Palczuk NC.Davis FF. J. Biol. Chem. 1977, 252: 3578 - 24
Caliceti P.Veronese FM. Adv. Drug Deliv. Rev. 2003, 55: 1261 - 25
Doyle MP.Hu W. J. Org. Chem. 2000, 65: 8839 - 26
Keegstra EMD.Zwikker JW.Roest MR.Jenneskens LW. J. Org. Chem. 1992, 57: 6678 - 27
Huynh THV.Mantel MLH.Mikkelsen K.Lindhardt AT.Nielsen NC.Otzen D.Skrydstrup T. Org. Lett. 2009, 1: 999 - 28
Fialkowski M.Bishop K. J. M.Klajn R.Smoukov SK.Campbell CJ.Grzybowski BA. J. Phys. Chem. B 2006, 110: 2482 - 29
French AC.Thompson AL.Davis BG. Angew. Chem. Int. Ed. 2009, 48: 1248