Download PDF
Synthesis 2012(5): 717-722  
DOI: 10.1055/s-0031-1289685
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Cost-Effective, Column-Free Route to Ethylene Glycol Oligomers EG6, EG10, and EG12

Chris M. Gothard, Bartosz A. Grzybowski*
Department of Chemistry, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208, USA
e-Mail: grzybor@northwestern.edu;
Further Information

Publication History

Received 5 October 2011
Publication Date:
03 February 2012 (online)

   Permissions and Reprints All articles of this category
Preview

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

    References

  • 1 Haag R. Kratz F. Angew. Chem. Int. Ed.  2006,  45:  1198 
    Search in Google Scholar
  • 2 Pirawattana T. Srinophakun T. Int. J. Mol. Sci.  2008,  9:  2290 
    Search in Google Scholar
  • 3 Palma JAD. Cleveland MV. McGowan J. Herrera JL. Am. J. Gastroenterol.  2007,  102:  1964 
    Search in Google Scholar
  • 4 Krause TL. Bittner GD. Proc. Natl. Acad. Sci. U.S.A.  1990,  87:  1471 
    Search in Google Scholar
  • 5 Corpet DE. Parnaud G. Delverdier M. Cancer Res.  2000,  60:  3160 
    Search in Google Scholar
  • 6 Rubio-Garcia J. Coppel Y. Lecante P. Mingotaud C. Chaudret B. Gauffre F. Kahn ML. Chem. Commun.  2011,  47:  988 
    Search in Google Scholar
  • 7 Ahmed SA. Tanaka M. J. Org. Chem.  2006,  71:  9884 
    Search in Google Scholar
  • 8 Andrus MB. Turner TM. Updegraff EP. Sauna ZE. Ambudkar SV. Tetrahedron Lett.  2001,  42:  3819 
    Search in Google Scholar
  • 9 Bartsch RA. Cason CV. Czech BP. J. Org. Chem.  1989,  54:  857 
    Search in Google Scholar
  • 10 Burkett BA. Chan TH. Synthesis  2004,  1007 
  • 11 Wilken J. Kent SBH. Curr. Opin. Biotechnol.  1998,  9:  412 
    Search in Google Scholar
  • 12 Knuf EC. Jiang J.-K. Gin MS. J. Org. Chem.  2003,  68:  9166 
    Search in Google Scholar
  • 13 Kochendoerfer GG. Curr. Opin. Chem. Biol.  2005,  9:  555 
    Search in Google Scholar
  • 14 Loiseau FA. Hii KKM. Hill AM. J. Org. Chem.  2004,  69:  639 
    Search in Google Scholar
  • 15 Lumpi D. Braunshier C. Hametner C. Horkel E. Zachhuber B. Lendl B. Fröhlich J. Tetrahedron Lett.  2009,  50:  6469 
    Search in Google Scholar
  • 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 
    Search in Google Scholar
  • 18 Pedrosa N. Pàmies JC. Coutinho JAP. Marrucho IM. Vega LF. Ind. Eng. Chem. Res.  2005,  44:  7027 
    Search in Google Scholar
  • 19 Pant HR. Bajgai MP. Nam KT. Chu KH. Park S.-J. Kim HY. Mater. Lett.  2010,  64:  2087 
    Search in Google Scholar
  • 20 Takahashi H. Kyu T. Trans-Cong Q. Yano O. Soen T. J. Polym. Sci., Part B: Poly. Phys.  1991,  29:  1419 
    Search in Google Scholar
  • 21 Zalipsky S. Adv. Drug Deliv. Rev.  1995,  16:  157 
    Search in Google Scholar
  • 22 Brocchini S. Godwin A. Balan S. Choi J.-w. Zloh M. Shaunak S. Adv. Drug Deliv. Rev.  2008,  60:  3 
    Search in Google Scholar
  • 23 Abuchowski A. van Es T. Palczuk NC. Davis FF. J. Biol. Chem.  1977,  252:  3578 
    Search in Google Scholar
  • 24 Caliceti P. Veronese FM. Adv. Drug Deliv. Rev.  2003,  55:  1261 
    Search in Google Scholar
  • 25 Doyle MP. Hu W. J. Org. Chem.  2000,  65:  8839 
    Search in Google Scholar
  • 26 Keegstra EMD. Zwikker JW. Roest MR. Jenneskens LW. J. Org. Chem.  1992,  57:  6678 
    Search in Google Scholar
  • 27 Huynh THV. Mantel MLH. Mikkelsen K. Lindhardt AT. Nielsen NC. Otzen D. Skrydstrup T. Org. Lett.  2009,  1:  999 
    Search in Google Scholar
  • 28 Fialkowski M. Bishop K. J. M. Klajn R. Smoukov SK. Campbell CJ. Grzybowski BA. J. Phys. Chem. B  2006,  110:  2482 
    Search in Google Scholar
  • 29 French AC. Thompson AL. Davis BG. Angew. Chem. Int. Ed.  2009,  48:  1248 
    Search in Google Scholar