Synlett 2014; 25(4): 523-526
DOI: 10.1055/s-0033-1340552
letter
© Georg Thieme Verlag Stuttgart · New York

Zn(OTf)2-Catalyzed Glycosylation of Glycals: Synthesis of 2,3-Unsaturated Glycosides via a Ferrier Reaction

Gundeboina Narasimha
D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
,
Batthula Srinivas
D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
,
Palakodety Radha Krishna*
D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
,
Sudhir Kashyap*
D-207, Discovery Laboratory, Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: skashyap@iict.res.in
› Author Affiliations
Further Information

Publication History

Received: 07 November 2013

Accepted after revision: 09 December 2013

Publication Date:
14 January 2014 (online)


Abstract

A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or ‘pseudo-glycals’ using Zn(OTf)2. Stereoselective glycosylation of glycal donor with various acceptors comprising of alcohols, phenols, thiols, and sugar aglycones proceeds smoothly to afford the corresponding 2,3-unsaturaed glycosides in good to excellent yields.

Supporting Information

 
  • References and Notes

  • 2 Review: Danishefsky SJ, Bilodeau MT. Angew. Chem., Int. Ed. Engl. 1996; 35: 1380
    • 3a Ferrier RJ. J. Chem. Soc. 1964; 5443
    • 3b Ciment DM. Ferrier R. J. J. Chem. Soc. C 1966; 441
    • 3c Ferrier RJ, Sankey GH. J. Chem. Soc. C 1966; 2345
    • 3d Ferrier RJ, Prasad N. J. Chem. Soc. C 1969; 570
  • 4 Williams NR, Wander JD. The Carbohydrates in Chemistry and Biochemistry . Academic Press; New York: 1980: 761
  • 5 Bussolo VD, Kim YJ, Gin DY. J. Am. Chem. Soc. 1998; 120: 13515
    • 6a Schmidt RR, Angerbauer R. Carbohydr. Res. 1981; 89: 159
    • 6b Angerbauer R, Schmidt RR. Carbohydr. Res. 1981; 89: 193
    • 6c Schmidt RR, Angerbauer R. Carbohydr. Res. 1979; 89: 272
    • 7a Schmidt RR, Angerbauer R. Angew. Chem., Int. Ed. Engl. 1977; 16: 783
    • 7b Durham TB, Miller MJ. Org. Lett. 2002; 4: 135
    • 7c Williams DR, Heidebrecht RW. Jr. J. Am. Chem. Soc. 2003; 125: 1843
    • 7d Panarese JD, Waters SP. Org. Lett. 2009; 11: 5086
    • 7e Rusin A, Zawisza-Puchalka J, Kujawa K, Gogler-Piglowska A, Wietrzyk J, Switalska M, Glowala-Kosinska M, Gruca A, Szeja W, Krawczyk Z, Grynkiewicz G. Bioorg. Med. Chem. 2011; 19: 295
    • 7f Bozell JJ, Tice NC, Sanyal N, Thompson D, Kim J.-M, Vidal S. J. Org. Chem. 2008; 73: 8763
    • 8a Tolstikov AG, Tolstikov GA. Russ. Chem. Rev. 1993; 62: 579
    • 8b Reddy BG, Vankar YD. Tetrahedron Lett. 2003; 44: 4765
    • 8c Lewis A, Stefanuti I, Swain SA, Smith SA, Taylor RJ. K. Tetrahedron Lett. 2001; 42: 5549
    • 8d Patterson L, Keown LE. Tetrahedron Lett. 1997; 38: 5727
    • 10a Borisova SA, Guppi SR, Kim HJ, Wu B, Penn JH, Liu H, O’Doherty GA. Org. Lett. 2010; 12: 5150
    • 10b Fraser-Reid B. Acc. Chem. Res. 1985; 18: 347
    • 10c Ferrier RJ. Adv. Carbohydr. Chem. Biochem. 1969; 24: 199
    • 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 Higashi K, Susaki H. Chem. Pharm. Bull. 1992; 40: 2019
    • 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
    • 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 Lopez JC, Gomez 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
    • 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
  • 15 See Supporting Information.
  • 16 Ramesh NG, Balasubramanian KK. Tetrahedron Lett. 1992; 33: 306