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Synthesis 2006(13): 2242-2250  
DOI: 10.1055/s-2006-942430
PAPER
© Georg Thieme Verlag Stuttgart · New York

Propane-1,3-diyl Dithioacetals of Carbohydrates; Part 7: Preparation of Aminocyclitols and Iminosugars by Intramolecular Cyclizations of d-Glucosamine Propane-1,3-diyl Dithioacetal Derivatives

Yue-Lei Chena,b, Robin Leguijta, Hartmut Redlich*a
a Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany
Fax: +49(251)839772; e-Mail: redlich@uni-muenster.de;
b NRW Graduate School of Chemistry, Corrensstraße 36, 48149 Münster, Germany
Further Information

Publication History

Received 27 April 2006
Publication Date:
24 June 2006 (online)

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Abstract

Versatile 3,4,5-tri-O-protected 2-acylamino-2-deoxy-6-O-tosyl-d-glucose propane-1,3-diyl dithioacetal intermediates were efficiently synthesized from d-glucosamine propane-1,3-diyl dithioacetal or its derivatives. Intramolecular cyclizations from these intermediates produced biologically important aminocyclitols as well as iminosugars. The 3,4-O-methylene protection on the intermediates did not hinder the cyclizations. The resultant aminocyclitols and iminosugars bearing orthogonal protecting groups are ideal for regioselective modification. Hence, deprotection methodology is also discussed.

Key words

chiral pool - intramolecular cyclizations - aminocyclitol - iminosugar - protecting-group cleavage

    References

  • See for example:
  • 1a Carbohydrate Mimics, Concepts and Methods   Chapleur Y. Wiley-VCH; Weinheim: 1998. 
    Google Scholar
  • 1b Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond   Stütz AE. Wiley-VCH; Weinheim: 1999. 
    Google Scholar
  • 1c Carbohydrates in Chemistry and Biology   Ernst B. Hart GW. Sinaӱ P. Wiley-VCH; Weinheim: 2000. 
    Google Scholar
  • 1d Carbohydrate-based Drug Discovery   Wong C.-H. Wiley-VCH; Weinheim: 2003. 
    Google Scholar
  • See the preceding papers:
  • 2a Chen Y.-L. Leguijt R. Redlich H. Synthesis  2006,  submitted 
    Google Scholar
  • 2b Chen Y.-L. Leguijt R. Redlich H. J. Carbohydr. Chem.  2006,  submitted 
    Google Scholar
  • 3a Krohn K. Börner G. J. Org. Chem.  1991,  56:  6038 
    CrossrefGoogle Scholar
  • 3b Krohn K. Börner G. J. Org. Chem.  1994,  59:  6063 
    CrossrefGoogle Scholar
  • 3c Krohn K. Gringard S. Börner G. J. Org. Chem.  1994,  59:  6069 
    CrossrefGoogle Scholar
  • 3d Krohn K. Gringard S. Börner G. Tetrahedron: Asymmetry  1994,  5:  2485 
    CrossrefGoogle Scholar
  • 4 Graham J. Ninan A. Reza K. Sainsbury M. Shertzer H. Tetrahedron  1992,  48:  167 
    CrossrefGoogle Scholar
  • 5 Redlich H. Sudau W. Szardenings AK. Vollerthun R. Carbohydr. Res.  1992,  226:  57 
    CrossrefPubMedGoogle Scholar