Trifluoroethylsulfonate protected monosaccharides in glycosylation reactions

Tetrahedron Letters

Volumn 45, Issue 34, 2004, Pages 6433-6437

  Karst, Nathalie A ^a   Islam, Tasneem F ^a   Avci, Fikri Y ^a,b   Linhardt, Robert J ^a,b  

^a E11 SSH   (United States)

^b RENSSELAER POLYTECHNIC INSTITUTE   (United States)

Author keywords

Glycosaminoglycans; Glycosylation; Trifluoroethylsulfonate

Indexed keywords

FLUORIDE; IMIDE; MONOSACCHARIDE; SULFIDE; SULFONIC ACID DERIVATIVE; TRIFLUOROETHYLSULFONATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 4143104605     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.131     Document Type: Article

References (18)

1. T. Islam, and R.J. Linhardt C.-H. Wong Carbohydrate-Based Drug Discovery Vol. 1 2003 Wiley-VCH Verlag-GmbH pp 407-433
2. F.Y. Avci, N. Karst, and R.J. Linhardt Curr. Pharm. Des. 9 2003 2323 2335
3. For reviews on GAGs see: N. Karst, and R.J. Linhardt Curr. Med. Chem. 10 2003 1993 2031
4. B.K.S. Yeung, P.Y.C. Chong, and P.A. Petillo J. Carbohydr. Chem. 21 2002 799 865
5. M.C. Hewitt, D.A. Snyder, and P.H. Seeberger J. Am. Chem. Soc. 124 2002 13434 13436
6. J.I. Tamura, K.W. Neumann, S. Kurono, and T. Ogawa Carbohydr. Res. 305 1998 43 63
7. N. Karst, and J.-C. Jacquinet Eur. J. Org. Chem. 2002 815 825
8. C.L. Penney, and A.S. Perlin Carbohydr. Res. 93 1981 241 246
9. A.D. Proud, J.C. Prodger, and S.L. Flitsch Tetrahedron Lett. 38 1997 7243 7246
10. N. Karst, T. Islam, and R.J. Linhardt Org. Lett. 5 2003 4839 4842
11. L. Yan, and D. Kahne J. Am. Chem. Soc. 118 1996 9239 9248
12. L. Jiang, and T.-H. Chan Tetrahedron Lett. 39 1998 355 358
13. 2,2,2-Trifluorodiazoethane solution in MeCN was prepared as described in Ref. 6. Caution: This reagent should be considered as potentially explosive and highly toxic
14. N. Karst, and J.-C. Jacquinet J. Chem. Soc., Perkin Trans. 1 2000 2709 2717
15. 3N, THF, 59%. See supplementary material
16. J. Gildersleeve, A. Smith, K. Sakurai, S. Raghavan, and D. Kahne J. Am. Chem. Soc. 121 1999 6176 6182
17. P. Konradsson, U.E. Udodong, and B. Fraser-Reid Tetrahedron Lett. 31 1990 4313 4316
18. J.D.C. Codée, R.E.J.N. Litjens, R. den Heeten, H.S. Overkleeft, J.H. van Boom, and G.A. van der Marel Org. Lett. 5 2003 1519 1522