Expedient and Facile One-Pot
Syntheses of Triazole-Linked Glycoconjugates under Microwave Irradiation

Swarbhanu Sarkar; Samrat Dutta; Asish Kumar Sen

doi:10.1055/s-0031-1289728

PAPER

Expedient and Facile One-Pot Syntheses of Triazole-Linked Glycoconjugates under Microwave Irradiation

Swarbhanu Sarkar, Samrat Dutta, Asish Kumar Sen*
Chemistry Division, Indian Institute of Chemical Biology, Council of Scientific and Industrial Research, 4, Raja S. C. Mullick Road, Jadavpur, Kolkata 700 032, India
Fax: +91(33)24735197; e-Mail: aksen@iicb.res.in;

Abstract

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Abstract

Effective microwave assisted one-pot syntheses of triazole-O-glycoconjugates and triazolylglycosides involving sequential glycosylation and click chemistry are described.

Key words

one-pot synthesis - triazole glycoconjugates - multi-component - glycosylation - click chemistry - microwave irradiation

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References

For reviews, see:

1a Sinay P. Hart GW. Ernst B. Carbohydrates in Chemistry and Biology Wiley-VCH; Weinheim: 2002.

1b Varki A. Essentials of Glycobiology 2nd ed.: Cold Spring Harbor Laboratory; New York: 1999.

1c Schofield L. Hewitt MC. Evans K. Siomos M.-A. Seeberger PH. Nature 2002, 418: 785

1d Fernandes B. Sagman U. Auger M. Demetrio M. Dennis JW. Cancer Res. 1991, 51: 718

1e Wharton SA. Weis W. Skehel DC. Wiley DC. The Influenza Virus Plenum; New York: 1989.

2a Yu H. Huang S. Chokhawala H. Sun M. Zheng H. Chen X. Angew. Chem. Int. Ed. 2006, 45: 3938

2b Dudkin VY. Crich D. Tetrahedron Lett. 2003, 44: 1787

2c Unverzagt C. Chem. Eur. J. 2003, 9: 1369

3a Houston TA. Blanchfield JT. Mini Rev. Med. Chem. 2003, 3: 669

3b Lillelund VH. Jensen HH. Liang X. Bols M. Chem. Rev. 2002, 102: 515

4 Wu P. Fokin VV. Aldrichimica Acta 2007, 40: 7

5a Rostovtsev VV. Green LG. Fokin VV. Sharpless KB. Angew. Chem. Int. Ed. 2002, 41: 2596

5b Tornøe CW. Christensen C. Meldal M. J. Org. Chem. 2002, 67: 3057

6 Alvarez R. Velazquez S. San-Felix A. Aquaro S. De Clercq E. Perno C.-F. Karlsson A. Balzarini J. Camarasa MJ. J. Med. Chem. 1994, 37: 4185

7 Buckle DR. Rockell CJM. Smith H. Spicer BA.
J. Med. Chem. 1986, 29: 2269

8 Genin MJ. Allwine DA. Anderson DJ. Barbachyn MR. Emmert DE. Garmon SA. Graber DR. Grega KC. Hester JB. Hutchinson DK. Morris J. Reischer RJ. Ford CW. Zurenko GE. Hamel JC. Schaadt RD. Stapert D. Yagi BH. J. Med. Chem. 2000, 43: 953

9 Wamhoff H. In Comprehensive Heterocyclic Chemistry Vol. 5: Katritzky AR. Rees CW. Pergamon; Oxford: p.669

10a Chan TR. Hilgraf R. Sharpless KB. Fokin VV. Org. Lett. 2004, 6: 2853

10b Meng J.-c. Fokin VV. Finn MG. Tetrahedron Lett. 2005, 46: 4543

10c Yousuf SK. Taneja SC. Mukherjee D. J. Org. Chem. 2010, 75: 3097

10d Tasdelen MA. Yagci Y. Tetrahedron Lett. 2010, 51: 6945

10e Sudhir VS. Phani Kumar NY. Chandrasekaran S. Tetrahedron 2010, 66: 1327

10f Moses JE. Moorhouse AD. Chem. Soc. Rev. 2007, 36: 1249

10g Iha RK. Wooley KL. Nystrom AM. Burke DJ. Kade MJ. Hawker CJ. Chem. Rev. 2009, 109: 5620

10h Katritzky A. Singh SK. J. Org. Chem. 2002, 67: 9077

10i Meldal M. Tornøe CW. Chem. Rev. 2008, 108: 2952

11 Sawa M. Hsu T.-L. Itoh T. Sugiyama M. Hanson SR. Vogt PK. Wong C.-H. Proc. Natl. Acad. Sci. U.S.A. 2006, 103: 12371

12 Wilkinson BL. Bornaghi LF. Houston TA. Innocenti A. Vullo D. Supuran CT. Poulsen SA. J. Med. Chem. 2007, 50: 1651

13 Lauren L. Rossi LL. Basu A. Bioorg. Med. Chem. Lett. 2005, 15: 3596

14 Kumar KK. Seenivasan SP. Kumar V. Das TM. Carbohydr. Res. 2011, 346: 2084

15 Schwardt O. Rabbani S. Hartmann M. Abgottspon D. Wittwer M. Kleeb S. Zalewski A. Smišeko M. Cutting B. Ernst B. Bioorg. Med. Chem. 2011, 19: 6454

16 dos Anjos JV. Filho RAWN. do Nascimento SC. Srivastava RM. de Melo SJ. Sinou D. Eur. J. Med. Chem. 2009, 44: 3571

17 Song Z. He X.-P. Li C. Gao L.-X. Wang Z.-X. Tang Y. Xie J. Li J. Chen G.-R. Carbohydr. Res. 2011, 346: 140

18 Appukkuttan P. Dehaen W. Fokin VV. van der Eycken E. Org. Lett. 2004, 6: 4223

19a Yoshimura Y. Shimizu H. Hinou H. Nishimura S.-I. Tetrahedron Lett. 2005, 46: 4701

19b Shimizu H. Yoshimura Y. Hinou H. Nishimura S.-I. Tetrahedron 2008, 64: 10091

20a Hiroshi Tanaka H. Adachi M. Tsukamoto H. Ikeda T. Yamada H. Takahashi T. Org. Lett. 2002, 4: 4213

20b Yamada H. Hayashi T. Carbohydr. Res. 2002, 337: 581

20c Wang Y. Huang X. Zhang L.-H. Ye X.-S. Org. Lett. 2004, 6: 4415

20d Yu B. Yang Z. Cao H. Curr. Org. Chem. 2005, 9: 179

21a Ferrier RJ. Furneaux RH. Meth. Carbohydr. Chem. 1980, 8: 251

21b Chen L. Zhu Y. Kong F. Carbohydr. Res. 2002, 337: 383

22a Chittaboina S. Xie F. Wang Q. Tetrahedron Lett. 2005, 46: 2331

22b Wilkinson BL. Bornaghi LF. Poulsen S.-A. Houston TA. Tetrahedron 2006, 62: 8115

23a Kumar R. Maulik PR. Misra AK. Glycoconjugate J. 2008, 25: 595

23b Kumar R. Tiwari P. Maulik PR. Misra AK. Eur. J. Org. Chem. 2006, 74

23c Kunz H. Sager W. Schanzenbach D. Decker M. Liebigs Ann. Chem. 1991, 649