Trimethylsilyl trifluoromethanesulfonate catalyzed nucleophilic substitution to give C- and N-glucopyranosides derived from d-glucopyranose

Synthesis

Volumn , Issue 19, 2007, Pages 3021-3031

  Oda, Yoshiki ^a   Yamanoi, Takashi ^a  

^a NOGUCHI INSTITUTE   (Japan)

Author keywords

D glucopyranose; Glycosides; Nucleophilic substitutions; Trifluoromethanesulfonate catalysis; Trimethylsilylated nucleophiles

Indexed keywords

D-GLUCOPYRANOSE; GLYCOSIDES; NUCLEOPHILIC SUBSTITUTIONS; TRIFLUOROMETHANESULFONATE CATALYSIS;

CARBON; CATALYSIS; STEREOSELECTIVITY; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

1 C ALLYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSE; 1 C BENZYL 2,3,4,6 TETRA O BENZYL ALPHA DEXTRO GLUCOPYRANOSE; 2 ALLYL 2 AZIDO 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYLTETRAHYDROPYRAN; 2 ALLYL 2 BENZYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYLTETRAHYDROPYRAN; 2 ALLYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 BUTYLTETRAHYDROPYRAN; 2 ALLYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 ETHYLTETRAHYDROPYRAN; 2 ALLYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 METHYLTETRAHYDROPYRAN; 2 ALLYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 PHENYLTETRAHYDROPYRAN; 2 ALLYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYLTETRAHYDROPYRAN 2 CARBONITRILE; 2 AZIDO 2 BENZYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYLTETRAHYDROPYRAN; 2 AZIDO 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 BUTYLTETRAHYDROPYRAN; 2 AZIDO 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 ETHYLTETRAHYDROPYRAN; 2 AZIDO 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 METHYLTETRAHYDROPYRAN; 2 AZIDO 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 PHENYLTETRAHYDROPYRAN; 2 BENZYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYLTETRAHYDROPYRAN 2 CARBONITRILE; 2,2 DIALLYL 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYLTETRAHYDROPYRAN; 2,3,4,6 TETRA O BENZYL 1 C BUTYL ALPHA DEXTRO GLUCOPYRANOSE; 2,3,4,6 TETRA O BENZYL 1 C ETHYL ALPHA DEXTRO GLUCOPYRANOSE; 2,3,4,6 TETRA O BENZYL 1 C METHYL ALPHA DEXTRO GLUCOPYRANOSE; 2,3,4,6 TETRA O BENZYL 1 C METHYL ALPHA DEXTRO GLUCOPYRANOSIDE; 2,3,4,6 TETRA O BENZYL 1 C PHENYL ALPHA DEXTRO GLUCOPYRANOSE; 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 BUTYLTETRAHYDROPYRAN 2 CARBONITRILE; 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 ETHYLTETRAHYDROPYRAN 2 CARBONITRILE; 3,4,5 TRIS(BENZYLOXY) 6 (BENZYLOXY)METHYL 2 METHYLTETRAHYDROPYRAN 2 CARBONITRILE; ACETONITRILE; GLUCOPYRANOSIDE; GLUCOPYRANOSYL ACETATE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID TRIMETHYLSILYL ESTER; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; GLYCOSIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 35349005332     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983882     Document Type: Article

References (22)

1. Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995.
2. For examples, see: (a) Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1998, 110, 470.
3. (b) Nicolaou, K. C.; Bunnage, M. K.; McGarry, D. G.; Shi, S.; Somers, P. K.; Wallace, P. A.; Chu, X.-J.; Agrios, K. A.; Gunzner, J. L.; Yang, Z. Chem. Eur. J. 1999, 5, 599.
4. (c) Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X.-Y.; Hwang, C.-K. J. Am. Chem. Soc. 1993, 115, 3558.
5. (d) Gomez, A. M.; Casillas, M.; Valverde, S.; Lopez, J. C. Tetrahedron: Asymmetry 2001, 12, 2175.
6. For examples, see: (a) Kraus, G. A.; Molina, M. T. J. Org. Chem. 1988, 53, 752.
7. (b) Czernecki, S.; Ville, G. J. Org. Chem. 1989, 54, 610.
8. For examples of reported C-glycosidation methods, see: (a) Chen, G.-R.; Fei, Z. B.; Huang, X.-T.; Xie, Y.-Y.; Xu, J.-L.; Gola, J.; Steng, M.; Praly, J.-P. Eur. J. Org. Chem. 2001, 2939.
9. (b) Gomez, A. M.; Uriel, C.; Jarosz, S.; Valverde, S.; Lopez, J. C. Eur. J. Org. Chem. 2003, 4830; and references cited therein.
10. For the reported O-glycosidation methods, see: (c) Yamanoi, T.; Oda, Y.; Matsuda, S.; Yamazaki, I.; Matsumura, K.; Katsuraya, K.; Watanabe, M.; Inazu, T. Tetrahedron 2006, 62, 10383.
11. (d) See also references cited in reference 4c.
12. (a) See reference 4c.
13. (b) Yamanoi, T.; Matsuda, S.; Yamazaki, I.; Inoue, R.; Hamasaki, K.; Watanabe, M. Heterocycles 2006, 68, 673.
14. (c) Yamanoi, T.; Inoue, R.; Matsuda, S.; Katsuraya, K.; Hamasaki, K. Tetrahedron: Asymmetry 2006, 17, 2914.
15. (d) Yamanoi, T.; Matsumura, K.; Matsuda, S.; Oda, Y. Synlett 2005, 2973.
16. (e) Yamanoi, T.; Oda, Y.; Yamazaki, I.; Shinbara, M.; Morimoto, K.; Matsuda, S. Lett. Org. Chem. 2005, 2, 242.
17. Yamanoi, T.; Oda, Y. Heterocycles 2002, 57, 229.
18. N1′-type reaction mechanism, see: Yamanoi, T.; Nara, Y.; Matsuda, S.; Oda, Y.; Yoshida, A.; Katsuraya, K.; Watanabe, M. Synlett 2007, 785.
19. Wenger, W.; Vasella, A. Helv. Chim. Acta 2000, 1542.
20. Yang, W.-B.; Yang, Y.-Y.; Gu, Y.-F.; Wang, S.-H.; Chang, C.-C.; Lin, C.-H. J. Org. Chem. 2002, 67, 3773.
21. Ellsworth, B. A.; Doyle, A. G.; Patel, M.; Caceres-Cortes, J.; Meng, W.; Deshpande, P. P.; Pullockaran, A.; Washburn, W. N. Tetrahedron: Asymmetry 2003, 14, 3243.
22. Li, X.; Ohtake, H.; Takahashi, H.; Ikegami, S. Tetrahedron 2001, 57, 4283.