Preparation of 2-deoxy-2-C-p-tolylsulfonyl-β-D-glucopyranosyl p-tolyl sulfones having non-chair conformation and their elimination reactions

Chemical Communications

Volumn , Issue 34, 2007, Pages 3568-3570

  Sakakibara, Tohru ^a   Suganuma, Tomomi ^a   Kajihara, Yasuhiro ^a  

^a YOKOHAMA CITY UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXY 2 C P TOLYLSULFONYL BETA DEXTRO GLUCOPYRANOSYL P TOLYL SULFONE; ACETIC ANHYDRIDE; HYDROXYL GROUP; SILICA GEL; SULFINIC ACID DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CONFORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE;

EID: 34748889933     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b707802a     Document Type: Article

References (19)

1. Carbohydrate Chemistry, ed., G.-J. Boons,, Blackie Academic & Professional, London, 1998, ch. 4 and 5
2. A. F. Bochkov and G. E. Zaikov, Chemistry of the O-glycosidic Bond, Pergamon Press, Oxford, 1979
3. D. G. Gorenstein J. B. Findlay B. A. Luxon D. Kar J. Am. Chem. Soc. 1977 99 3473
4. A. J. Kirby Acc. Chem. Res. 1984 17 305
5. C. W. Andrews J. P. Bowen B. Fraser-Reid J. Chem. Soc., Chem. Commun. 1989 1913
6. C. W. Andrews B. Fraser-Reid J. B. Bowen J. Am. Chem. Soc. 1991 113 8293
7. M. L. Sinnott, The Anomeric Effect and Associated Stereoelectronic Effects, in ACS Symp. Ser. 539, ed., G. R. J. Thatcher,, ACS, Washington, DC, 1992, ch. 6, pp. 97-113
8. P. Deslongchamps, Organic Chemistry Series, Vol. 1: Stereoelectronic Effects in Organic Chemistry, Pergamon Press, Oxford, 1983
9. C. G. Suresh B. Ravindran K. N. Rao T. Pathak Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2000 C56 1030
10. R. Kuroki L. H. Weaver B. W. Matthews Science 1993 262 2030
11. D. S. Brown S. V. Ley S. Vile M. Thompson Tetrahedron 1991 47 1329
12. T. Sakakibara K. Suzuki A. Sakai M. Shindo C. Nagano S. Narumi Y. Kajihara K. Mochizuki Tetrahedron Lett. 2003 44 5711
13. I. P. Smoliakova R. Caple D. Gregory J. Org. Chem. 1995 60 1221
14. H. Abe M. Terauchi A. Matsuda S. Shuto J. Org. Chem. 2003 68 7439
15. E. J. Corey G. Sarakinos A. Fischer Tetrahedron Lett. 1999 40 7745
16. S. J. Angyal Angew. Chem., Int. Ed. Engl. 1969 8 157
17. R. U. Lemieux T. L. Nagabhushan S. W. Gunner Can. J. Chem. 1968 46 405
18. S. V. Ley H. W. M. Priepke S. L. Warriner Angew. Chem., Int. Ed. Engl. 1994 33 2290
19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, J. L. Andres, M. Head-Gordon, E. S. Replogle and J. A. Pople, GAUSSIAN 98 (Revision A.9), Gaussian, Inc., Pittsburgh, PA, 1998