Download PDF
Synlett 2003(6): 0809-0812
DOI: 10.1055/s-2003-38726
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

New Polymer-Supported Allyloxycarbonyl (Alloc) and Propargyloxycarbonyl (Proc) Amino-Protecting Reagents

Rafael Chinchilla, David J. Dodsworth, Carmen Nájera*, José M. Soriano
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apartado 99, 03080 Alicante, Spain
Fax: +34(96)5903549; e-Mail: cnajera@ua.es;
Further Information

Publication History

Received 21 January 2003
Publication Date:
17 April 2003 (online)

    Permissions and Reprints All articles of this category

Abstract

New polymer-supported reagents, Alloc-P-OSu and Proc-P-OSu, have been prepared from a polymeric N-hydroxysuccinimide (P-HOSu), and used as solid-supported reagents for the allyloxycarbonyl (Alloc) and propargyloxycarbonyl (Proc) protection of the amino group. These new polymeric reagents are safe and stable, the residual P-HOSu generated after the protection reaction can be easily separated by simple filtration and reused.

Key words

amino acids - polymers - protecting reagents - solid-supported reagents

    References

  • 1a Green TW. Wuts PGM. Protective Groups in Organic Synthesis   J. Wiley & Sons; New York: 1999.  p.526-528  
    Crossref
  • 1b Kocienski PJ. Protecting Groups   Thieme; Stuttgart: 1994.  p.199-202  
    Crossref
  • 1c Bodanszky M. Bodanszky A. The Practice of Peptide Synthesis   Springer; Berlin: 1984. 
    Crossref
  • 1d Albericio F. Biopolymers (Peptide Science)  2000,  55:  123 
    CrossrefSearch in Google Scholar
  • 2 Stevens CM. Watanabe R. J. Am. Chem. Soc.  1950,  72:  725 
    CrossrefSearch in Google Scholar
  • Some examples:
  • 3a Paulsen H. Merz G. Brockhausen I. Liebigs Ann. Chem.  1990,  719 
  • 3b Attal S. Bay S. Cantacuzene D. Tetrahedron  1992,  48:  9251 
    Search in Google Scholar
  • 3c Unverzagt C. Kunz H. Bioorg. Med. Chem.  1994,  2:  1189 
    Search in Google Scholar
  • 3d Meinjohanns E. Vargas-Berenguel A. Meldal M. Paulsen H. Bock K. J. Chem. Soc., Perkin Trans. 1  1995,  2165 
  • 4a Sinha S. Ilankumaran P. Chandrasekaran S. Tetrahedron Lett.  1999,  40:  771 
    Search in Google Scholar
  • 4b Fukase Y. Fukase K. Kusumoto S. Tetrahedron Lett.  1999,  40:  1169 
    Search in Google Scholar
  • 4c Fukase Y. Fukase K. Kusumoto S. Pept. Sci.  1999,  36:  93 
    Search in Google Scholar
  • 4d Bhat RG. Sinha S. Chandrasekaran S. Chem. Commun.  2002,  812 
  • 4e Bhat RG. Kérourédan E. Porhiel E. Chandrasekaran S. Tetrahedron Lett.  2002,  43:  2467 
    Search in Google Scholar
  • 5 Herrinton PM. In Encyclopedia of Reagents for Organic Synthesis   Paquette LA. John Wiley & Sons Ltd.; Chichester: 1995.  p.95-96  
  • 6 Sennyey G. Barcelo G. Senet J.-P. Tetrahedron Lett.  1987,  28:  5811 
    Search in Google Scholar
  • 7 Blaakmeer J. Tijsse-Klasen T. Tesser GI. Int. J. Pept. Protein Res.  1991,  37:  556 
    Search in Google Scholar
  • 8 Hayakawa Y. Kato H. Uchiyama M. Kajino H. Noyori R. J. Org. Chem.  1986,  51:  2400 
    CrossrefSearch in Google Scholar
  • 9 Takeda K. Tsuboyama K. Hoshino M. Kishino M. Ogua H. Synthesis  1987,  557 
    Thieme Connect
  • For recent reviews on polymer-supported chemistry see:
  • 11a Hermkens PHH. Ottenheijm HCJ. Rees DC. Tetrahedron  1996,  52:  4527 
    Search in Google Scholar
  • 11b Früchtel JS. Jung G. Angew. Chem., Int. Ed. Engl.  1996,  35:  17 
    Search in Google Scholar
  • 11c Hermkens PHH. Ottenheijm HCJ. Rees DC. Tetrahedron  1997,  53:  5643 
    Search in Google Scholar
  • 11d Brown R. Contemp. Org. Synth.  1997,  216 
  • 11e Gravert DJ. Janda KD. Chem. Rev.  1997,  97:  489 
    Search in Google Scholar
  • 11f Shuttleworth SJ. Allin SM. Sharma PK. Synthesis  1997,  1217 
  • 11g Lorsbach BA. Kurth MJ. Brown RCD. J. Chem. Soc., Perkin Trans. 1  1998,  3293 
  • 11h Hermkens PHH. Ottenheijm HCJ. Rees DC. Synlett  1998,  817 
  • 11i Wenworth R. Janda KD. Chem. Commun.  1999,  1917 
  • 11j Brown AR. Chem. Rev.  1999,  99:  1549 
    Search in Google Scholar
  • 11k James IW. Tetrahedron  1999,  55:  4855 
    Search in Google Scholar
  • 11l Shuttleworth SJ. Allin SM. Wilson RD. Nasturica D. Synthesis  2000,  1035 
  • 11m Ley SV. Baxendale IR. Bream RN. Jackson PS. Leach AG. Longbottom DA. Nesi M. Scott JS. Storer RI. Taylor SJ. J. Chem. Soc., Perkin Trans. 1  2000,  3815 
  • 11n Orain D. Ellard J. Bradley M. J. Comb. Chem.  2002,  4:  1 
    Search in Google Scholar
  • 12 Chinchilla R. Dodsworth DJ. Nájera C. Soriano JM. Tetrahedron Lett.  2001,  42:  4487 
    CrossrefSearch in Google Scholar
  • 13a Chinchilla R. Dodsworth DJ. Nájera C. Soriano JM. Tetrahedron Lett.  2001,  42:  7579 
    CrossrefSearch in Google Scholar
  • 13b Chinchilla R, Dodsworth DJ, Nájera C, Soriano JM, and Yus M. inventors; ES  P200101169. 
    Crossref
  • 14 Chinchilla R. Dodsworth DJ. Nájera C. Soriano JM. Bioorg. Med. Chem. Lett.  2002,  12:  1817 
    Search in Google Scholar
  • 15 Chinchilla R. Dodsworth DJ. Nájera C. Soriano JM. Tetrahedron Lett.  2003,  44:  463 
    Search in Google Scholar
  • 16 The loading of P-HOSu(9) was 1.0 mmol/g, as it was determined by the assay of the OH group content: Dendrinos KG. Jeong J. Huang W. Kalivretenos AG. Chem. Commun.  1998,  499 
    Crossref
10

Novabiochem (2002/3 catalogue: 5 g, 162 ).

17

Available from MEDALCHEMY S. L.