Download PDF
Synthesis 2009(15): 2596-2604  
DOI: 10.1055/s-0029-1217403
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Glycosylations of Tertiary Alcohols: Synthesis of Fully Protected Disaccharides with Sterically Demanding Groups Attached to the Sugar Core

Annika Holkenbrink, Jordi Bertrán Vicente, Daniel B. Werz*
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Fax: +49(551)399476; e-Mail: dwerz@gwdg.de;
Further Information

Publication History

Received 18 February 2009
Publication Date:
22 June 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Modified gluco- and galactopyranosides with sterically demanding groups in the 4-position were synthesized. Glycosylation studies of these tertiary alcohols with glycosyl trichloroacet­imidates and glycosyl phosphates were performed. Despite steric hindrance the modified disaccharide moieties could be assembled in moderate yields.

Key words

carbohydrates - glycosylation - steric hindrance - glycosides

    References

  • 1a Varki A. Glycobiology  1993,  3:  97 
    Google Scholar
  • 1b Lis H. Sharon N. Eur. J. Biochem.  1993,  218:  1 
    Google Scholar
  • 1c Dwek RA. Chem. Rev.  1996,  96:  683 
    Google Scholar
  • 1d Lee YC. Lee RT. Acc. Chem. Res.  1995,  28:  322 
    Google Scholar
  • 1e Werz DB. Seeberger PH. Chem. Eur. J.  2005,  11:  3194 
    Google Scholar
  • 1f Seeberger PH. Werz DB. Nature  2007,  446:  1046 
    Google Scholar
  • 2a Choudhury B. Leoff C. Saile E. Wilkins P. Quinn CP. Kannenberg EL. Carlson RW. J. Biol. Chem.  2006,  281:  27932 
    Google Scholar
  • 2b Oberli MA. Bindschädler P. Werz DB. Seeberger PH. Org. Lett.  2008,  10:  905 
    Google Scholar
  • 3a Karlsson KA. Biochem. Soc. Trans.  1999,  27:  471 
    Google Scholar
  • 3b Karlsson KA. Adv. Exp. Med. Biol.  2001,  491:  431 
    Google Scholar
  • 3c Tamborrini M. Werz DB. Frey J. Pluschke G. Seeberger PH. Angew. Chem. Int. Ed.  2006,  45:  6581 ; Angew. Chem. 2006, 118, 6731
    Google Scholar
  • 3d Seeberger PH. Werz DB. Nature Rev. Drug Discovery  2005,  4:  751 
    Google Scholar
  • 4a Herget S. Toukach PV. Ranzinger R. Hull WE. Knirel YA. von der Lieth C.-W. BMC Struct. Biol.  2008,  8:  35 
    Google Scholar
  • 4b Werz DB. Ranzinger R. Herget S. Adibekian A. von der Lieth C.-W. Seeberger PH. ACS Chem. Biol.  2007,  2:  685 
    Google Scholar
  • 5a Thibodeaux CJ. Melançon CE. Liu H.-w. Nature  2007,  446:  1008 
    Google Scholar
  • 5b Chatterjee D. Bozic C. Aspinall GO. Brennan PJ. J. Biol. Chem.  1988,  263:  4092 
    Google Scholar
  • 6 Qian X. Sujino K. Otter A. Palcic MM. Hindsgaul O. J. Am. Chem. Soc.  1999,  121:  12063 
    CrossrefGoogle Scholar
  • For 1-adamantanol as acceptor several examples are known:
  • 7a Crich D. Sun S. J. Am. Chem. Soc.  1998,  120:  435 
    Google Scholar
  • 7b Crich D. Yao Q. Org. Lett.  2003,  5:  2189 
    Google Scholar
  • 7c Babu RS. O’Doherty GA. J. Am. Chem. Soc.  2003,  125:  12406 
    Google Scholar
  • 7d Okada Y. Mukae T. Okajima K. Taira M. Fujita M. Yamada H. Org. Lett.  2007,  9:  1573 
    Google Scholar
  • 7e Baek JY. Choi TJ. Jeon HB. Kim KS. Angew. Chem. Int. Ed.  2006,  45:  7436 ; Angew. Chem. 2006, 118, 7596
    Google Scholar
  • 8a Ernst C. Piacenza M. Grimme S. Klaffke W. Carbohydr. Res.  2003,  338:  231 
    Google Scholar
  • 8b Shao H. Ekthawatchai S. Wu S.-H. Zou W. Org. Lett.  2004,  6:  3497 
    Google Scholar
  • 8c Elamparuthi E. Linker T. Org. Lett.  2008,  10:  1361 
    Google Scholar
  • 8d Al-Harrasi A. Reissig H.-U. Angew. Chem. Int. Ed.  2005,  44:  6227 ; Angew. Chem. 2005, 117, 6383
    Google Scholar
  • 8e Yin J. Linker T. Chem. Eur. J.  2009,  15:  49 
    Google Scholar
  • 8f Pfrengle F. Lentz D. Reißig H.-U. Angew. Chem. Int. Ed.  2009,  48:  3165 ; Angew. Chem. 2009, 121, 3211
    Google Scholar
  • 9 Kahne D. Walker S. Cheng Y. van Engen D. J. Am. Chem. Soc.  1989,  111:  6881 
    CrossrefGoogle Scholar
  • 10 For an overview, see: Lutz J.-F. Angew. Chem. Int. Ed.  2007,  46:  1018 ; Angew. Chem. 2007, 119, 1036
    CrossrefPubMedGoogle Scholar
  • 11 For an overview, see: Chinchilla R. Najera C. Chem. Rev.  2007,  107:  874 
    Google Scholar
  • 12 Preuss R. Jung K.-H. Schmidt RR. Liebigs Ann. Chem.  1992,  377 
    CrossrefGoogle Scholar
  • 13a Zhu X. Schmidt RR. Angew. Chem. Int. Ed.  2009,  48:  1900 ; Angew. Chem. 2009, 121, 1932
    Google Scholar
  • 13b Codée JDC. Seeberger PH. ACS Symp. Ser.  2007,  960:  150 
    Google Scholar
  • 14 Schmidt RR. Kinzy W. Adv. Carbohydr. Chem. Biochem.  1994,  50:  21 
    PubMedGoogle Scholar
  • 15 The compounds 5a and 5b were synthesized before, but analytical data were not given: Jensen HH. Bols M. Org. Lett.  2003,  5:  3419 
    CrossrefGoogle Scholar
  • 16 A mixture of compounds 8a and 8b was synthesized before, but analytical data were not given: Daly SM. Armstrong RW. Tetrahedron Lett.  1989,  30:  5713 
    CrossrefGoogle Scholar