N-Glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl azide

Carbohydrate Research

Volumn 341, Issue 9, 2006, Pages 1081-1090

  Temelkoff, David P ^a   Zeller, Matthias ^a   Norris, Peter ^a  

^a YOUNGSTOWN STATE UNIVERSITY   (United States)

Author keywords

Dipolar cycloaddition; N Glycoside; Neoglycotrimer; Staudinger reaction

Indexed keywords

ACETYLATION; ACTIVATION ANALYSIS; AMINO ACIDS; MOLECULAR STRUCTURE; REACTION KINETICS;

DIPOLAR CYCLOADDITION; N-GLYCOSIDE; NEOGLYCOTRIMER; STAUDINGER REACTION;

SUGARS;

1,2,3 TRIAZOLE DERIVATIVE; 2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL AZIDE; AMIDE; AZIDE; BROMIDE; GLYCOSIDE; SUGAR; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CRYSTALLOGRAPHY; HYBRID; PRIORITY JOURNAL; SEPARATION TECHNIQUE; STAUDINGER REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS;

AZIDES; CARBOHYDRATE CONFORMATION; GLUCOSE; GLYCOSIDES; TRISACCHARIDES;

TETRA;

EID: 33747464388     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.04.011     Document Type: Article

References (34)

1. Fuchs E.-F., and Lehmann J. Chem. Ber. 108 (1975) 2254-2260
2. Nicolaou K.C., Flörke H., Egan M.G., Barth T., and Estevez V.A. Tetrahedron Lett. 36 (1995) 1775-1778
3. Suhara Y., Hildreth J.E.K., and Ichikawa Y. Tetrahedron Lett. 37 (1996) 1575-1578
4. Estevez J.C., Burton J.W., Estevez R.J., Ardron H., Wormald M.R., Dwek R.A., Brown D., and Fleet G.W.J. Tetrahedron: Asymmetry 9 (1998) 2137-2154
5. Smith M.D., Long D.D., Martín A., Marquess D.G., Claridge T.D.W., and Fleet G.W.J. Tetrahedron Lett. 40 (1999) 2191-2194
6. Long D.D., Hungerford N.L., Smith M.D., Brittain D.E.A., Marquess D.G., Claridge T.D.W., and Fleet G.W.J. Tetrahedron Lett. 40 (1999) 2195-2198
7. Claridge T.D.W., Long D.D., Hungerford N.L., Aplin R.T., Smith M.D., Marquess D.G., and Fleet G.W.J. Tetrahedron Lett. 40 (1999) 2199-2202
8. Moreno-Vargas A.J., Fernández-Bolaños J.G., Fuentes J., and Robina I. Tetrahedron Lett. 42 (2001) 1283-1285
9. Mayes B.A., Simon L., Watkin D.J., Ansell C.W.G., and Fleet G.W.J. Tetrahedron Lett. 45 (2004) 157-162
10. Mayes B.A., Stetz R.J.E., Watterson M.P., Edwards A.A., Ansell C.W.G., Tranter G.E., and Fleet G.W.J. Tetrahedron: Asymmetry 15 (2004) 627-638
11. Smith M.D., Claridge T.D.W., Tranter G.E., Sansom M.S.P., and Fleet G.W.J. Chem. Commun. (1998) 2041-2042
12. Hungerford N.L., Claridge T.D.W., Watterson M.P., Aplin R.T., Moreno A., and Fleet G.W.J. J. Chem. Soc., Perkin Trans. 1 40 (2000) 3666-3679
13. Baron R., Bakowies D., and van Gunsteren W.F. Angew. Chem., Int. Ed. 43 (2004) 4055-4059
14. Edwards A.A., Fleet G.W.J., Mayes B.A., Hunter S.J., and Tranter G.E. Chirality 17 (2005) S114-S119
15. Smith M.D., Claridge T.D.W., Sansom M.S.P., and Fleet G.W.J. Org. Biomol. Chem. 1 (2003) 3647-3655
16. Baron R., Bakowies D., and van Gunsteren W.F. J. Peptide Sci. 11 (2005) 74-84
17. Styron S.D., Kiely D.E., and Ponder G. J. Carbohydr. Chem. 22 (2003) 123-142
18. Deras I.L., Takegawa K., Kondo A., Kato I., and Lee Y.C. Bioorg. Med. Chem. Lett. 8 (1998) 1763-1766
19. Temelkoff D.P., Norris P., and Zeller M. Acta Crystallogr. Sect. E: Struct. Rep. Online E60 (2004) 1975-1976
20. Temelkoff, D. P.; Smith, C. R.; Kibler, D. A.; McKee, S.; Duncan, S. J.; Zeller, M.; Hunsen, M.; Norris, P. Carbohydr. Res., in press.
21. Tosin M., and Murphy P.V. Org. Lett. 4 (2002) 3675-3678
22. Kovács L., O{combining double acute accent}sz E., Domokos V., Holzer W., and Gyo{combining double acute accent}rgydeák Z. Tetrahedron 57 (2001) 4609-4621
23. Bianchi A., Russo A., and Bernardi A. Tetrahedron: Asymmetry 16 (2005) 381-386
24. Miner P.L., Wagner T.R., and Norris P. Heterocycles 65 (2005) 1035-1049
25. Akula R.A., Temelkoff D.P., Artis N.D., and Norris P. Heterocycles 63 (2004) 2719-2725
26. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
27. For examples, see:. Hotha S., and Kashyap S. J. Org. Chem. 71 (2006) 364-367
28. Marmuse L., Nepogodiev S.A., and Field R.A. Org. Biol. Chem. 3 (2005) 2225-2227
29. Tørnoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
30. Pérez-Balderas F., Ortega-Muñoz M., Morales-Sanfrutos J., Hernández-Mateo F., Calvo-Flores F.G., Calvo-Asin J.A., Isac-Garcia J., and Santoyo-González F. Org. Lett. 5 (2003) 1951-1954
31. Kolb H.C., and Sharpless K.B. Drug Discovery Today 8 (2003) 1128-1137
32. smart. Software for the CCD Detector System, version 5.630; Bruker AXS: Madison, WI, 2002.
33. saint+. Data Processing Software for the CCD Detector System, version 6.45; Bruker AXS: Madison, WI, 2003.
34. shelxtl. Software Package for the Refinement of Crystal Structures, version 6.10; Bruker AXS: Madison, WI, 2000.