RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2014; 46(09): 1191-1196
DOI: 10.1055/s-0033-1340873
DOI: 10.1055/s-0033-1340873
paper
Synthesis of 2,3-Unsaturated Glycosides and Disaccharides via Ruthenium(III) Chloride Catalyzed Ferrier Glycosylation
Weitere Informationen
Publikationsverlauf
Received: 10. Dezember 2013
Accepted after revision: 06. Februar 2014
Publikationsdatum:
05. März 2014 (online)
Abstract
A facile and stereoselective method for Ferrier glycosylation was developed using ruthenium(III) chloride. Using this protocol, the glycal donor reacted smoothly with several acceptors comprising different functionalities to afford corresponding 2,3-unsaturated glycosides in good to excellent yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are general synthesis information and 1H and 13C NMR spectra of all the compounds
- Supporting Information
-
References
- 1 Williams NR, Wander JD. The Carbohydrates in Chemistry and Biochemistry . Academic Press; New York: 1980
- 2 Bussolo VD, Kim YJ, Gin DY. J. Am. Chem. Soc. 1998; 120: 13515
- 3a Schmidt RR, Angerbauer R. Carbohydr. Res. 1981; 89: 159
- 3b Angerbauer R, Schmidt RR. Carbohydr. Res. 1981; 89: 193
- 3c Schmidt RR, Angerbauer R. Carbohydr. Res. 1979; 72: 272
- 4 Schmidt RR, Angerbauer R. Angew. Chem. Int. Ed. 1977; 16: 783
- 5a Tolstikov AG, Tolstikov GA. Russ. Chem. Rev. 1993; 62: 579
- 5b Reddy BG, Vankar YD. Tetrahedron Lett. 2003; 44: 4765
- 5c Lewis A, Stefanuti I, Swain SA, Smith SA, Taylor RJ. K. Tetrahedron Lett. 2001; 42: 5549
- 5d Patterson L, Keown LE. Tetrahedron Lett. 1997; 38: 5727
- 6a Chambers DJ, Evans GR, Fairbanks AJ. Tetrahedron: Asymmetry 2005; 16: 45
- 6b Dorgan BJ, Jackson RF. W. Synlett 1996; 859
- 7a Schreiber SL. Science (Washington, D.C.) 2000; 287: 1964
- 7b Hotha S, Tripathi A. J. Comb. Chem. 2005; 7: 968
- 8 Review: Danishefsky SJ, Bilodeau MT. Angew. Chem. Int. Ed. 1996; 35: 1380
- 9a Ferrier R. J. Chem. Soc. 1964; 5443
- 9b Ciment DM, Ferrier R. J. Chem. Soc. C 1966; 441
- 9c Ferrier RJ, Sankey GH. J. Chem. Soc. C 1966; 2345
- 10a Ferrier RJ, Prasad N. J. Chem. Soc. C 1969; 570
- 10b Ferrier RJ, Prasad N. J. Chem. Soc. C 1969; 581
- 10c Review: Gómez AM, Lobo F, Uriel C, López JC. Eur. J. Org. Chem. 2013; 7221
- 10d Review: McKay MJ, Nguyen HM. ACS Catal. 2012; 2: 1563
- 11a Babu BS, Balasubramanian KK. Tetrahedron Lett. 2000; 41: 1271
- 11b Masson C, Soto J, Bessodes M. Synlett 2000; 1281
- 11c Takhi M, Abdel-Rahman AA.-H, Schmidt RR. Synlett 2001; 427
- 11d Swamy NR, Venkateswarlu Y. Synthesis 2002; 598
- 11e Hotha S, Tripathi A. Tetrahedron Lett. 2005; 46: 4555
- 11f Bettadaiah BK, Srinivas P. Tetrahedron Lett. 2003; 44: 7257
- 11g Kim H, Men H, Lee C. J. Am. Chem. Soc. 2004; 126: 1336
- 11h Swamy NR, Srinivasulu M, Reddy TS, Goud TV, Venkateswarlu Y. J. Carbohydr. Chem. 2004; 23: 435
- 11i Rafiee E, Tangestaninejad S, Habibi MH, Mirkhani V. Bioorg. Med. Chem. Lett. 2004; 14: 3611
- 11j Babu JL, Khare A, Vankar YD. Molecules 2005; 10: 884
- 11k Naik PU, Nara JS, Harjani JR, Salunkhe MM. J. Mol. Catal. A: Chem. 2005; 234: 35
- 11l Procopio A, Dalposso R, De Nino A, Nardi M, Oliverio M, Russo B. Synthesis 2006; 2608
- 11m Procopio A, Dalpozzo R, De Nino A, Maiuolo L, Nardi M, Oliverio M, Russo B. Carbohydr. Res. 2007; 342: 2125
- 11n Balamurugan R, Kopollu SR. Tetrahedron 2009; 65: 8139
- 11o Rodriguez OM, Colinas PA, Bravo RD. Synlett 2009; 1154
- 11p Gorityala BK, Lorpitthaya R, Bai Y, Liu X.-W. Tetrahedron 2009; 65: 5844
- 11q Nagaraj P, Ramesh NG. Tetrahedron Lett. 2009; 50: 3970
- 11r Chen P.-R, Wang S.-S. Tetrahedron 2012; 68: 5356
- 11s Freitas JC. R, Couto TR, Paulino AA. S, de Freitas Filho JR, Malvestiti I, Oliveira RA, Menezes PH. Tetrahedron 2012; 68: 10611
- 11t Descotes G, Martin J.-C. Carbohydr. Res. 1977; 56: 168
- 11u Bhate P, Horton D, Priebe W. Carbohydr. Res. 1985; 144: 331
- 11v Zhang G, Shi L, Liu Q, Wang J, Li L, Liu X. Tetrahedron 2007; 63: 9705
- 11w Zhang G, Liu Q. Synth. Commun. 2007; 37: 3485
- 11x Tayama E, Otoyama S, Isaka W. Chem. Commun. 2008; 4216
- 11y Ding F, William R, Gorityala BK, Ma J, Wang S, Liu X.-W. Tetrahedron Lett. 2010; 51: 3146
- 11z Chen P.-R, Lin L. Tetrahedron 2013; 69: 10045
- 12a Gorityala BK, Cai S, Lorpitthaya R, Ma J, Pasunooti KK, Liu X.-W. Tetrahedron Lett. 2009; 50: 676
- 12b Zhou J, Zhang B, Yang G, Chen X, Wang Q, Wang Z, Zhang J, Tang J. Synlett 2010; 893
- 12c Hadfield AF, Sartorelli AC. Carbohydr. Res. 1982; 101: 197
- 12d Engler TA, Letavic MA, Combrink KD, Takusagawa F. J. Org. Chem. 1990; 55: 5812
- 12e Yadav JS, Satyanarayana M, Balanarsaiah E, Raghavendra S. Tetrahedron Lett. 2006; 47: 6095
- 12f Agarwal A, Rani S, Vankar YD. J. Org. Chem. 2004; 69: 6137
- 12g Misra AK, Tiwari P, Agnihotri G. Synthesis 2005; 260
- 12h Chen P.-R, Wang S.-S. Tetrahedron 2013; 69: 583
- 12i Chen P.-R, Lin L. Tetrahedron 2013; 69: 4524
- 12j Rosati O, Curini M, Messina F, Marcotullio MC, Cravotto G. Catal. Lett. 2013; 143: 169
- 13a Toshima K, Ishizuka T, Matsuo G, Nakata M, Kinoshita M. J. Chem. Soc., Chem. Commun. 1993; 704
- 13b Sobti A, Sulikowski GA. Tetrahedron Lett. 1994; 35: 3661
- 13c Koreeda M, Houston TA, Shull BK, Klemke E, Tuinman RJ. Synlett 1995; 90
- 13d López JC, Gómez AM, Valverde S, Fraser-Reid B. J. Org. Chem. 1995; 60: 3851
- 13e De K, Legros J, Crousse B, Bonnet-Delpon D. Tetrahedron 2008; 64: 10497
- 13f Mukherjee A, Jayaraman N. Carbohydr. Res. 2011; 346: 1569
- 14a Hotha S, Kashyap S. J. Am. Chem. Soc. 2006; 128: 9620
- 14b Hotha S, Kashyap S. Tetrahedron Lett. 2006; 47: 2021
- 14c Kashyap S, Vidadala SR, Hotha S. Tetrahedron Lett. 2007; 48: 8960
- 14d Vidadala SR, Thadke SA, Hotha S, Kashyap S. J. Carbohydr. Chem. 2012; 31: 241
- 14e Hotha S, Kashyap S. J. Org. Chem. 2006; 71: 364
- 14f Narasimha G, Srinivas B, RadhaKrishna P, Kashyap S. Synlett 2014; 25: 523
- 15 Srinivas, B.; Radha Krishna, P.; Kashyap, S. manuscript in preparation.