Studies of S -But-3-ynyl and gem -dimethyl S -But-3-ynyl thioglycoside donors in gold-catalyzed glycosylations

Journal of Carbohydrate Chemistry

Volumn 32, Issue 5-6, 2013, Pages 336-359

  Adhikari, Surya ^a   Li, Xiaohua ^a   Zhu, Jianglong ^a  

^a UNIVERSITY OF TOLEDO   (United States)

Author keywords

Alkyne; Catalysis; Glycosylation; Gold; Oligosaccharide synthesis

Indexed keywords

EID: 84884575800     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328303.2013.831433     Document Type: Article

References (39)

1. Varki, A. Biological roles of oligosaccharides: all of the theories are correct. Glycobiology 1993, 3, 97-130
2. Bertozzi, C.R.; Kiessling, L.L. Chemical glycobiology. Science 2001, 291, 2357-2364
3. Ranade, S.C.; Demchenko, A.V. Mechanism of chemical glycosylation: focus on the mode of activation and departure of anomeric leaving groups. J. Carbohydr. Chem. 2013, 32, 1-43
4. Zhu, X.; Schmidt, R.R. New principles for glycoside-bond formation. Angew. Chem. Int. Edit. 2009, 48, 1900-1934
5. Demchenko, A.V., Ed. Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance. Wiley-VCH: Weinheim, Germany, 2008, 501 pp
6. Fuegedi, P. Glycosylation methods. The Organic Chemistry of Sugars, Levy, D.E., Fuegedi, P., Eds. CRC Press: Boca Raton, FL. 2006, pp. 89-179
7. Galoníc, D.P.; Gin, D.Y. Chemical glycosylation in the synthesis of glycoconjugate antitumour vaccines. Nature 2007, 446, 1000-1007
8. Toshima, K.; Tatsuta, K. Recent progress in O-glycosylation methods and its application to natural products synthesis. Chem. Rev. 1993, 93, 1503-1531
9. Li, X.; Zhu, J. Recent advances in transition metal-catalyzed O-glycosylations. J. Carbohydr. Chem. 2012, 31, 284-324
10. McKay, M.J.; Nguyen, H.M. Recent advances in transition metal-catalyzed glycosylation. ACS Catal. 2012, 2, 1563-1595
11. Yu, B.; Sun, J.; Yang, X. Assembly of naturally occurring glycosides, evolved tactics, and glycosylation methods. Acc. Chem. Res. 2012, 45, 1227-1236
12. Yang, F.; Wang, Q.; Yu, B. ortho-Alkynylphenyl thioglycosides as a new type of glycosylation donors under the catalysis of Au(I) complexes. Tetrahedron Lett. 2012, 53, 5231-5234
13. Li, Y.; Yang, X.; Liu, Y.; Zhu, C.; Yang, Y.; Yu, B. Gold(I)-catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors: general scope and application in the synthesis of a cyclic triterpene saponin. Chem. Eur. J. 2010, 16, 1871-1882
14. Li, Y.; Yang, Y.; Yu, B. An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf. Tetrahedron Lett. 2008, 49, 3604-3608
15. Kayastha, A.K.; Hotha, S. Versatile gold catalyzed transglycosidation at ambient temperature. Chem. Comm. 2012, 48, 7161-7163
16. Sureshkumar, G.; Hotha, S. Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides. Tetrahedron Lett. 2007, 48, 6564-6568
17. Hotha, S.; Kashyap, S. Propargyl glycosides as stable glycosyl donors: anomeric activation and glycoside syntheses. J. Am. Chem. Soc. 2006, 128, 9620-9621
18. Adhikari, S.; Baryal, K.N.; Zhu, D.; Li, X.; Zhu, J. Gold-catalyzed synthesis of 2-deoxy glycosides using S-but-3-ynyl thioglycoside donors. ACS Catal. 2012, 3, 57-60
19. For our recent work in stereoselective synthesis of S-linked 2-deoxy glycosides (2-deoxy thioglycosides), see: Baryal, K.N.; Zhu, D.; Li, X.; Zhu, J. Angew. Chem., Int. Edit. 2013, 52, 8012-8016
20. Journet, M.; Rouillard, A.; Cai, D.; Larsen, R.D. Double radical cyclization/?-fragmentation of acyclic ?-yne vinyl sulfides. Synthesis of 3-vinyldihydrothiophene and dihydrothiopyran derivatives. A new example of a 5-endo-trig radical cyclization. J. Org. Chem. 1997, 62, 8630-8631
21. 2,2-Dimethyl-3-butyn-1-thiol 7 was prepared from 2,2-dimethyl-3-butyn-1-ol following the same procedure for the preparation of 3-butyn-1-thiol 6 as in ref 8. See Experimental section for details
22. Fortin, M.; Kaplan, J.; Pham, K.; Kirk, S.; Andrade, R.B. For use of gem-dimethyl 4-pentenyl glycosides in carbohydrate synthesis, see: gem-Dimethyl 4-pentenyl glycosides: novel glycosylating agents and anomeric protecting groups. Org. Lett. 2009, 11, 3594-3597
23. Wang, W.; Hammond, G.B.; Xu, B. Ligand effects and ligand design in homogeneous gold(I) catalysis. J. Am. Chem. Soc. 2012, 134, 5697-5705
24. Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. AuCl3-catalyzed benzannulation: synthesis of naphthyl ketone derivatives from oalkynylbenzaldehydes with alkynes. J. Am. Chem. Soc. 2002, 124, 12650-12651
25. Zhu, J.; Germain, A.R.; Porco, J.A., Jr. Synthesis of azaphilones and related molecules by employing cycloisomerization of o-alkynylbenzaldehydes. Angew. Chem. Int. Edit. 2004, 43, 1239-1243
26. Shi, Z.; He, C. For previous reports using a combination of AuCl3 and 3 AgOTf for preparation of more reactive Au(III) complex in 1,2-dichloroethane, see: An Aucatalyzed cyclialkylation of electron-rich arenes with epoxides to prepare 3-chromanols. J. Am. Chem. Soc. 2004, 126, 5964-5965
27. Shi, Z.; He, C. Direct functionalization of arenes by primary alcohol sulfonate esters catalyzed by gold(III). J. Am. Chem. Soc. 2004, 126, 13596-13597
28. Reetz, M.T.; Sommer, K. In addition, Reetz and coworkers observed an interesting experimental outcome using nitromethane as solvent, see: Gold-catalyzed hydroarylation of alkynes. Eur. J. Org. Chem. 2003, 3485-3496
29. Previously, we found that AgOTf by itself did not activate 2-deoxy S-but-3-ynyl thioglycoside donors for the synthesis of 2-deoxy sugars
30. Sammes, P.G.; Weller, D.J. Steric promotion of ring formation. Synthesis 1995, 1205-1222, and references cited therein
31. See Experimental section for details
32. Corma, A.; Gonźalez-Arellano, C.; Iglesias, M.; Śanchez, F. Efficient synthesis of vinyl and alkyl sulfides via hydrothiolation of alkynes and electron-deficient olefins using soluble and heterogenized gold complexes catalysts. Appl. Catal. A 2010, 375, 49-54
33. Trost, B.M.; Hu, Y.; Horne, D.B. Total synthesis of (+)-frondosin A. Application of the Ru-catalyzed [5+2] cycloaddition. J. Am. Chem. Soc. 2007, 129, 11781-11790
34. Lu, S.R.; Lai, Y.H.; Chen, J.H.; Liu, C.Y.; Mong, K.K.T. Dimethylformamide: an unusual glycosylation modulator. Angew. Chem. Int. Edit. 2011, 50, 7315-7320
35. Maity, S.K.; Basu, N.; Ghosh, R. Efficient activation of thioglycosides with N-(pmethylphenylthio)-?-caprolactam-TMSOTf. Carbohyd. Res. 2012, 354, 40-48
36. Vidadala, S.R.; Hotha, S., Methyl glycosides are identified as glycosyl donors for the synthesis of glycosides, disaccharides and oligosaccharides. Chem. Comm. 2009, 2505-2507
37. Zhu, Y.; Yu, B., Characterization of the isochromen-4-yl-gold (I) intermediate in the gold (I)-catalyzed glycosidation of glycosyl ortho-alkynylbenzoates and enhancement of the catalytic efficiency thereof. Angew. Chem. Int. Edit. 2011, 123, 8479-8482
38. Mehta, S.; Pinto, B.M. Tris(4-bromophenyl)aminium hexachloroantimonatemediated glycosylations of selenoglycosides and thioglycosides. Evidence for single electron transfer? Carbohyd. Res. 1998, 310(1), 43-51
39. Marra, A.; Esnault, J.; Veyrieres, A.; Sinay, P. Isopropenyl glycosides and congeners as novel classes of glycosyl donors: theme and variations. J. Am. Chem. Soc. 1992, 114, 6354-6360.