Modification of methyl O-propargyl-d-glucosides: model studies for the synthesis of alkynyl based functional polysaccharides

Carbohydrate Research

Volumn 342, Issue 14, 2007, Pages 2031-2048

  Tankam, Pascal F ^a   Mischnick, Petra ^a   Hopf, Henning ^a   Jones, Peter G ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Acetylenic carbohydrates; Glucan derivatives; Propargyl ethers; X ray crystallography

Indexed keywords

ACETYLENIC CARBOHYDRATES; GLUCAN DERIVATIVES; PROPARGYL ETHERS;

ALKALINITY; DERIVATIVES; FUNCTIONAL GROUPS; MOLECULAR STRUCTURE; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

POLYSACCHARIDES;

ACETYLENE DERIVATIVE; ALDEHYDE DERIVATIVE; ALKYNYL GROUP; AZIDE; BENZYL AZIDE; CARBROMAL; ESTER DERIVATIVE; GLUCAN; GLYCOSIDASE; METHYL 4,6 O BENZYLIDENE 2,3 DI O PROPARGYL ALPHA DEXTRO GLUCOSIDE; METHYL O PROPARGYL DEXTRO GLUCOSIDE; POLYSACCHARIDE; TRIAZOLE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; MANNICH REACTION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKYNES; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; METHYLGLUCOSIDES; MOLECULAR STRUCTURE; POLYSACCHARIDES;

EID: 34547191149     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2007.05.007     Document Type: Article

References (31)

1. Mischnick P., Heinrich J., Gohdes M., Wilke O., and Rogmann N. Macromol. Chem. Phys. 201 (2001) 1985-1995
2. Dubber M., and Lindhorst T.K. Carbohydr. Res. 310 (1998) 35-41
3. Wenz G., and Höfler Th. Carbohydr. Res. 322 (1999) 153-165
4. Slaghek, T. M.; Timmermans, J. W.; Fester, G. K. Patent WO0187986, 2001, CAN 136:7993.
5. Belghiti T., Joly J.-P., Didierjeau C., Dahaoi S., and Chapleur Y.S. Tetrahedron 43 (2002) 1441-1443
6. Aversa M.C., Barattucci A., Bilardo M.C., Bonaccorsi P., Fiannetto P., Rollin P., and Tatibouët A. J. Org. Chem. 70 (2005) 7389-7396
7. Bernet B., and Vasella A. Acetylenosaccharides. In: Diederich F., Stang P.J., and Tykwinski R.R. (Eds). Acetylene Chemistry. Chemistry, Biology and Material Science (2005), Wiley-VCH 174-231
8. Alzee J., Cai C., and Vasella A. Helv. Chim. Acta 78 (1995) 242-264
9. Murty K.V.S.N., Xie T., Bernet B., and Vasella A. Helv. Chim. Acta 89 (2006) 675-730
10. Hoffmann B., Bernet B., and Vasella A. Helv. Chim. Acta 85 (2002) 265-287
11. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
12. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
13. Wilkinson B.L., Bornaghi L.F., Poulsen S.-A., and Houston T.A. Tetrahedron 62 (2006) 8115-8125
14. Bock V.D., Hiemstra H., and van Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68 and references cited therein
15. Hasegawa T., Umeda M., Numata M., Li C., Bae A.-H., Fujisawa T., Haraguchi S., Sakurai K., and Shinkai S. Carbohydr. Res. 341 (2006) 35-40
16. Dörner S., and Westermann B. Chem. Commun. (2005) 2852-2854
17. Tankam, P. F.; Müller, R.; Mischnick, P.; Hopf, H. Carbohydr. Res., in press, doi:10.1016/j.carres.2007.05.017.
18. Evans M.E. Carbohydr. Res. 21 (1972) 473-475
19. Wu X., Kong F., Lu D., and Li G. Carbohydr. Res. 235 (1992) 163-178
20. Bieber L.W., and Da Silva M.F. Tetrahedron Lett. 45 (2004) 8281-8283
21. Bodine K.D., Gin D.Y., and Gin M.S. J. Am. Chem. Soc. 126 (2004) 1638-1639
22. Himo F., Lovell T., Hilgraf R., Rostovtsev V.V., Noodleman L., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 210-216
23. Rodionov V.O., Fokin V.V., and Finn M.G. Angew. Chem. 117 (2005) 2250-2255
24. Angew. Chem., Int. Ed. 44 (2005) 2210-2215
25. Wu P., Feldman A.K., Nugent A.F., Hawker C.J., Scheel A., Voit B., Pyun J., Fréchet J.M.J., Sharpless K.B., and Fokin V.V. Angew. Chem. 116 (2004) 4018-4022
26. Angew. Chem., Int. Ed. 43 (2004) 3928-3932
27. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem. 114 (2002) 2708-2711
28. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
29. Kochetkov N.K., and Chizhov O.S. Adv. Carbohydr. Chem. 21 (1966) 39-93
30. Kochetkov N.K., and Chizhov O.S. Tetrahedron 21 (1965) 2029-2047
31. Bosso C., Defaye J., Gadelle A., and Ulrich J. Org. Mass Spectrom. 12 (1977) 493-499