β-selective C-mannosylation of electron-rich phenols

Synthesis

Volumn , Issue 14, 2010, Pages 2393-2398

  Weck, Stefan ^a   Opatz, Till ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

anomers; C glycosides; glycosylation; Lewis acids; phenols

Indexed keywords

ANOMERS; C-GLYCOSIDES; ELECTRON-RICH PHENOLS; LEWIS ACID; LEWIS ACIDS;

ACIDS; ESTERIFICATION; GLYCOSYLATION; SUGARS;

PHENOLS;

1 (2',3',4',6' TETRA O BENZYL ALPHA DEXTRO GALACTOPYRANOSYL)NAPHTHALEN 2 OL; 1 (2',3',4',6' TETRA O BENZYL ALPHA DEXTRO MANNOPYRANOSYL)NAPHTHALEN 2 OL; 1 (2',3',4',6' TETRA O BENZYL BETA DEXTRO MANNOPYRANOSYL)NAPHTHALEN 2 OL; 1 (2',3',4',6' TETRA O BENZYL BETA DEXTRO MANNOPYRANOSYL)NAPHTHALENE 2,7 DIOL; 2 (2',3',4',6' TETRA O BENZYL BETA DEXTRO MANNOPYRANOSYL) 3,5 DIMETHOXYPHENOL; 2 (2',3',4',6' TETRA O BENZYL BETA DEXTRO MANNOPYRANOSYL) 4,5 DIMETHOXYPHENOL; 2 (2',3',4',6' TETRA O BENZYL BETA DEXTRO MANNOPYRANOSYL) 5 METHOXYPHENOL; 2 NAPHTHOL; 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO MANNOPYRANOSYL TRICHLOROACETIMIDATE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DEGRADATION; GLYCOSYLATION; HYDROLYSIS; KOENIGS KNORR REACTION; MANNOSYLATION; PROCESS OPTIMIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 77954568460     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218772     Document Type: Article

References (33)

1. Gridley J J., Osborn H M. I., J. Chem. Soc., Perkin Trans. 1 2000 1471
2. Barresi F, Hindsgaul O, J. Am. Chem. Soc. 1991 113 9376
3. Stork G, Kim G, J. Am. Chem. Soc. 1992 114 1087
4. Ito Y, Ogawa T, Angew. Chem., Int. Ed. Engl. 1994 33 1765
5. Angew. Chem. 1994, 106, 1843
6. Kunz H, Günther W, Angew. Chem., Int. Ed. Engl. 1988 27 1086
7. Angew. Chem. 1988, 100, 1118
8. Paulsen H, Angew. Chem., Int. Ed. Engl. 1982 21 155; Angew. Chem. 1982, 94, 184
9. Crich D, Sun S, J. Am. Chem. Soc. 1998 120 435
10. Codee J D. C., Hossain L H., Seeberger P H., Org. Lett. 2005 7 3251
11. Bililign T, Griffith B R., Thorson J S., Nat. Prod. Rep. 2005 22 742
12. Jaramillo C, Knapp S, Synthesis 1994 1
13. Du Y, Linhardt R J., Vlahov I R., Tetrahedron 1998 54 9913
14. Schmidt R R., Effenberger G, Carbohydr. Res. 1987 171 59
15. Matsumoto T, Katsuki M, Suzuki K, Tetrahedron Lett. 1988 29 6935
16. Palmacci E R., Seeberger P H., Org. Lett. 2001 3 1547
17. Ben A, Yamauchi T, Matsumoto T, Suzuki K, Synlett 2004 225
18. Li Y, Wei G, Yu B, Carbohydr. Res. 2006 341 2717
19. Matsumoto T, Hosoya T, Suzuki K, Synlett 1991 709
20. Kometani T, Kondo H, Fujimori Y, Synthesis 1988 1005
21. Mahling J A., Schmidt R R., Synthesis 1993 325
22. Schmidt R R., Michel J, Angew. Chem., Intl. Ed. Engl. 1980 19 731
23. Angew. Chem. 1980, 92, 763
24. Schmidt R R., Hoffmann M, Tetrahedron Lett. 1982 23 409
25. Jeelnik M, Plavec J, Polanc S, Koevar M, Carbohydr. Res. 2000 328 591
26. Lindhorst T K., Essentials of Carbohydrate Chemistry and Biochemistry 3rd ed. Wiley-VCH Weinheim, 2007
27. Lönn H, Carbohydr. Res. 1985 139 105
28. Grathwohl M, Schmidt R R., Synthesis 2001 2263
29. Eichler E, Jennings H J., Gilbert M, Whitfield D M., Carbohydr. Res. 1999 319 1
30. Schmidt R R., Michel J, Roos M, Liebigs Ann. Chem. 1984 1343
31. 4 conformer. See:, Paulsen H, Györgydeák Z, Friedmann M, Chem. Ber. 1974 107 1590
32. Finch P, Nagpurkar A G., Carbohydr. Res. 1976 49 275
33. Laschat S, Kunz H, J. Org. Chem. 1991 56 5883