Synthesis of Divalent 2,2′-Linked Mannose Derivatives by Homodimerization

Abstract

Several studies have implicated (1→2)-linked mannans as biologically relevant compounds. Recently, there has been a growing interest in the synthesis of multivalent carbohydrate assemblies due to their ability to target multiple receptors simultaneously. In the present work, a protective group strategy, based on the methodology originally developed by Crich, has been utilized for the homodimerization of olefinic carbohydrates, allowing a highly diastereoselective synthesis of some divalent structures. Furthermore, it is shown that divalent donors may undergo coupling reactions without losses in stereoselectivity or efficiency. The strategies described may potentially be applied to the synthesis of diverse neoglycoconjugates and oligosaccharides.

Key words

carbohydrates - divalent molecules - diastereoselective synthesis - homodimerization - (1→2)-linked mannans

References

• 1 Dalle F. Jouault T. Trinel PA. Esnault J. Mallet JM. d’Athins P. Poulain D. Bonnin A. Infect. Immun.  2003,  71:  7061 
• 2 Bewley CA. Kiyonaka S. Hamachi I. J. Mol. Biol.  2002,  322:  881 
• 3 Sandström C. Berteau O. Gemma E. Oscarson S. Kenne L. Gronenborn AM. Biochemistry  2004,  43:  13926 
• 4 Jouault T. Lepage G. Bernigaud A. Trinel P.-A. Fradin C. Wieruszeski J.-M. Strecker G. Poulain D. Infect. Immun.  1995,  63:  2378 
• 5 Li R.-K. Cutler JE. J. Biol. Chem.  1993,  268:  18293 
• 6 Miyakawa Y. Kuribayashi T. Kagaya K. Suzuki M. Nakase T. Fukazawa Y. Infect. Immun.  1992,  60:  2493 
• 7 Kiessling LL. Gestwicki JE. Strong LE. Curr. Opin. Chem. Biol.  2000,  4:  696 
• 8 Hayes W. Osborn HMI. Osborne SD. Rastall RA. Romagnoli B. Tetrahedron  2003,  59:  7983 
• 9 Roy R. Das SK. Santoyo-González F. Hernández-Mateo F. Dam TK. Brewer CF. Chem. Eur. J.  2000,  6:  1757 
• 10 Roy R. Dominique R. Das SK. J. Org. Chem.  1999,  64:  5408 
• 11 Jörgensen M. Hadwiger P. Madsen R. Stütz AE. Wrodnigg TM. Curr. Org. Chem.  2000,  4:  565 
• 12 Roy R. Das SK. Chem. Commun.  2000,  519 
• 13 Crich D. Jayalath P. Hutton T. J. Org. Chem.  2006,  71:  3064 
• 14 Crich D. Chandrasekera NS. Angew. Chem. Int. Ed.  2004,  43:  5386 
• 15 Toshima K. Tatsuta K. Chem. Rev.  1993,  93:  1503 
• 16 Osborn HMI. Carbohydrates   Elsevier Science Ltd.; Oxford: 2003.  p.147-165  
• 17 Osborn HMI. Carbohydrates   Elsevier Science Ltd.; Oxford: 2003.  p.22-27  
• 18 Cai J. Davison BE. Ganellin CR. Thaisrivongs S. Tetrahedron Lett.  1995,  36:  6535 
• 19 Crich D. Jayalath P. Org. Lett.  2005,  7:  2277 
• 20 Dominique R. Das SK. Roy R. Chem. Commun.  1998,  2437 
• 21 Cho JH. Kim BM. Org. Lett.  2003,  5:  531 
• 22 Haack KL. Ahn YM. Georg GI. Mol. Diversity  2005,  9:  301 
• 23 Galan BR. Kalbarczyk KP. Szczepankiewicz S. Keister JB. Diver ST. Org. Lett.  2007,  9:  1203 
• 24 Berkowitz DB. Maiti G. Charette BD. Dreis CD. MacDonald RG. Org. Lett.  2004,  6:  4921 
• 25 Postema MHD. Piper JL. Tetrahedron Lett.  2002,  43:  7095 
• 26 Boons G.-J. Hale KJ. Organic synthesis with carbohydrates   Sheffield University Press; England: 2000.  p.103 
• 27 Stork G. La Clair JL. J. Am. Chem. Soc.  1996,  118:  247 
• 28 Crich D. Smith M. J. Am. Chem. Soc.  2001,  123:  9015 
• 29 Fürstner A. Jeanjean F. Razon P. Wirtz C. Mynott R. Chem. Eur. J.  2003,  9:  307 
• 30The synthesis and analytical data of these compounds are discussed in a separate paper see:
• 30 Poláková M. Roslund MU. Ekholm FS. Saloranta T. Leino R. Eur. J. Org. Chem.  2009,  in press; DOI: 10.1002/ejoc.200801024 
• 31 Leeuwenburg MA. van der Marel GA. Overkleeft HS. Curr. Opin. Chem. Biol.  2003,  7:  757 
• 32 Boger DL. Honda T. J. Am. Chem. Soc.  1994,  116:  5647 
• 33 Ren T. Liu D. Tetrahedron Lett.  1999,  40:  7621 
• 34a Jung ME. Clevenger GL. Tetrahedron Lett.  1991,  32:  6089 
• 34b Blattner R. Furneaux RH. Ludewig M. Carbohydr. Res.  2006,  341:  299