Synthesis of New Optically Active d-Glucosamine-Pyrrole Derivatives

Abstract

From d-glucosamine hydrochloride was synthesized, for the first time, three new optically active derivatives of d-glucosamine-pyrrole with the pyrrole group unsubstituted in the 2- and 5-positions. New N-benzylpyrrole-d-glucosamine derivatives were also prepared from the same substrate.

Key words

glycosides - heterocycles - pyrroles - chirality - d-glucosamine

References

• 1 Vernin G. Chemistry of Heterocyclic Compounds in Flavours and Aromas   Ellis Horwood Ltd.; London: 1982. 
• 2 Gribble GW. In Comprehensive Heterocyclic Chemistry II   Katritzky AR. Rees CW. Scriven EFV. Elsevier; London: 1996.  p.211-257  
• 3 Heinze J. Top. Curr. Chem.  1990,  152:  1 
• 4 Heinze J. In Encyclopedia of Electrochemistry   Vol. 8:  Bard AJ. Stratmann M. Wiley-VCH; Weinheim: 2004.  Chap. 16.
• 5 Salmon M. Aguilar MM. Curr. Top. Electrochem.  1994,  3:  53 
• 6 Nonaka T. In Organic Electrochemistry   Lund H. Baizer MM. Marcel Dekker; New York: 1991.  3rd ed.. p.1131 
• 7 Nonaka T. Abe S. Fuchigami T. Bull. Chem. Soc. Jpn.  1983,  56:  2778 
• 8 Komori T. Nonaka T. J. Am. Chem. Soc.  1984,  106:  2656 
• 9 Schwientek M. Pleus S. Hamann CH. J. Electroanal. Chem.  1999,  461:  94 
• 10 Moutet J.-C. Saint-Aman E. Tran-Van F. Angibeaud P. Utille J.-P. Adv. Mater. (Weinheim, Ger.)  1992,  4:  511 
• 11 Pleus S. Schwientek M. Synth. Met.  1998,  95:  233 
• 12 Stefan R.-I. Aboul-Enein HY. van Staden JF. Sensors Update  2002,  10:  123 
• 13 Ichikawa Y. Ohara F. Kotsuki H. Nakano K. Org. Lett.  2006,  8:  5009 
• 14 Kunz H. Rück K. Angew. Chem., Int. Ed. Engl.  1993,  32:  336 
• 15 Bowers SG. Coe DM. Boons G.-J. J. Org. Chem.  1998,  63:  4570 
• 16 Irving JC. Earl JC. J. Chem. Soc.  1922,  2376 
• 17a Bergmann M. Zervas L. Ber. Dtsch. Chem. Ges. B  1931,  64:  975 
• 17b White T. J. Chem. Soc.  1938,  1498 
• 18 Jefford CW. Sienkiewicz K. Thornton SR. Helv. Chim. Acta  1995,  78:  1511 
• 19 Kawana M. Emoto S. Bull. Chem. Soc. Jpn.  1969,  42:  3539 
• 20a Nicolaou KC. Estrada AA. Zak M. Lee SH. Safina BS. Angew. Chem. Int. Ed.  2005,  44:  1378 
• 20b Nicolaou KC. Bulger PG. Brenzovich WE. Org. Biomol. Chem.  2006,  4:  2158 
• 21 Dawe RD. Fraser-Reid B. J. Org. Chem.  1984,  49:  522 
• 22 Allevi P. Anastasia M. Ciuffreda P. Fiecchi A. Scala A. J. Chem. Soc., Perkin Trans. 1  1989,  1275 
• 23 Bellamy F. Ou K. Tetrahedron Lett.  1984,  25:  839 

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Crystallographic data for compound 5 were deposited at the Cambridge Crystallographic Data Centre with deposit number CCDC-644070.