Regioselective Phthalimidopropyl-Modification of Carbohydrates in One Step

Christoph D. Heidecke; Thisbe K. Lindhorst

doi:10.1055/s-2005-921753

PAPER

Regioselective Phthalimidopropyl-Modification of Carbohydrates in One Step

Christoph D. Heidecke, Thisbe K. Lindhorst*
Otto Diels-Institute of Organic Chemistry, Christiana Albertina University Kiel, Otto-Hahn-Platz 3, 24098 Kiel, Germany
Fax: +49(431)8807410; e-Mail: tklind@oc.uni-kiel.de;

Abstract

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Abstract

A series of regioselectively 3-O-(3-phthalimidopropyl)-modified sugars was synthesized in a one-step procedure using bis-dibutyltin oxide and 3-bromopropyl phthalimide. This process offers a short access to the corresponding amino-functionalized carbohydrates, which are versatile building blocks for the synthesis of glycomimetics.

Key words

carbohydrates - glycosides - protecting groups - regioselectivity - glycomimetics

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References

1a Ziegler T. In Carbohydrate Chemistry Boons G.-J. Chapman; London: 1998. p.21

1b Kunz H. Waldmann H. In Comprehensive Organic Synthesis Vol. 6: Trost BM. Fleming I. Pergamon; Oxford: 1991. p.631

1c McGeary RP. Jablonkai I. Toth I. Tetrahedron 2001, 57: 8733

1d Dubber M. Lindhorst TK. Org. Lett. 2001, 3: 4019

1e Gruner SAW. Locardi E. Lohof E. Kessler H. Chem. Rev. 2002, 102: 491

1f Ghosh M. Dulina RG. Kakarla R. Sofia MJ. J. Org. Chem. 2000, 65: 8387

1g Davis BG. Chem. Rev. 2002, 102: 579

2 Lee X. Thompson A. Zhang Z. Ton-that H. Biesterfeldt J. Ogata C. Xu L. Johnston RAZ. Young NM. J. Biol. Chem. 1998, 273: 6312

3 Sarkar M. Wu AM. Kabat EA. Arch. Biochem. Biophys. 1981, 209: 204

4 Young NM. Johnston RAZ. Szabo AG. Watson DC. Arch. Biochem. Biophys. 1989, 270: 596

5a David S. Thieffry A. Veyrières A. J. Chem. Soc., Perkin Trans. 1 1981, 1796

5b David S. Hanessian S. Tetrahedron 1985, 41: 643

6a Manoharan M. Tivel KL. Andrade LK. Cook PD. Tetrahedron Lett. 1995, 36: 3647

6b Hwang J.-T. Greenberg MM. J. Org. Chem. 2001, 66: 363

7a Nagashima N. Ohno M. Chem. Lett. 1987, 141

7b Izumi M. Suhara Y. Ichikawa Y. J. Org. Chem. 1998, 63: 4811

8 Griffey RH. Monia BP. Cummins LL. Freier S. Greig MJ. Guinosso CJ. Lesnik E. Manalili SM. Mohan V. Owens S. Ross BR. Sasmor H. Wancewicz E. Weiler K. Wheeler PD. Cook PD. J. Med. Chem. 1996, 39: 5100

9 Wang L.-X. Lee YC. J. Chem. Soc., Perkin Trans. 1 1996, 581

10 Zehavi U. Sharon N. J. Org. Chem. 1972, 37: 2141

11 Rainer H. Scharf H.-D. Runsink J. Liebigs Ann. Chem. 1992, 103