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 Chen; Robin Leguijt; Hartmut Redlich

doi:10.1055/s-2006-942430

PAPER

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 Chen^a,b, Robin Leguijt^a, 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

Abstract

All articles of this category

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

Full Text

References

See for example:

1a Carbohydrate Mimics, Concepts and Methods Chapleur Y. Wiley-VCH; Weinheim: 1998.

1b Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond Stütz AE. Wiley-VCH; Weinheim: 1999.

1c Carbohydrates in Chemistry and Biology Ernst B. Hart GW. Sinaӱ P. Wiley-VCH; Weinheim: 2000.

1d Carbohydrate-based Drug Discovery Wong C.-H. Wiley-VCH; Weinheim: 2003.

See the preceding papers:

2a Chen Y.-L. Leguijt R. Redlich H. Synthesis 2006, submitted

2b Chen Y.-L. Leguijt R. Redlich H. J. Carbohydr. Chem. 2006, submitted

3a Krohn K. Börner G. J. Org. Chem. 1991, 56: 6038

3b Krohn K. Börner G. J. Org. Chem. 1994, 59: 6063

3c Krohn K. Gringard S. Börner G. J. Org. Chem. 1994, 59: 6069

3d Krohn K. Gringard S. Börner G. Tetrahedron: Asymmetry 1994, 5: 2485

4 Graham J. Ninan A. Reza K. Sainsbury M. Shertzer H. Tetrahedron 1992, 48: 167

5 Redlich H. Sudau W. Szardenings AK. Vollerthun R. Carbohydr. Res. 1992, 226: 57