Stereoselective synthesis of α- and β-C-glucosides via radical cyclization with an allylsilyl tether. Control of the stereoselectivity by changing the conformation of the pyranose ring

Tetrahedron Letters

Volumn 41, Issue 21, 2000, Pages 4151-4155

  Shuto, Satoshi ^a   Terauchi, Masaru ^a   Yahiro, Yumi ^a   Abe, Hiroshi ^a   Ichikawa, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1ALPHA GLUCOSIDE; 1BETA GLUCOSIDE; GLUCOSIDE; HYDROXYL GROUP; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0034729165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00556-6     Document Type: Article

References (23)

1. (a) Berridge, M. J. Nature 1993, 361, 315-325.
2. (b) Potter, B. V. L; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933-1972, and references cited therein.
3. (a) Tatani, K.; Shuto, S.; Ueno, Y.; Matsuda, A. Tetrahedron Lett. 1998, 39, 5065-5068.
4. (b) Shuto, S.; Tatani, K.; Ueno, Y.; Matsuda, A. J. Org. Chem. 1998, 63, 8815-8824.
5. (c) Kashiwayanagi, M.; Tatani, K.; Shuto, S.; Matsuda, A. Eur. J. Neurosci. 2000, 12, 606-612.
6. (d) Abe, H.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 2000, 41, 2391-2394.
7. (a) Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
8. (b) Jaramillo, C.; Knapp S. Synthesis 1994, 1-20.
9. (c) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995.
10. (d) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Rato, 1995.
11. (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett. 1998, 700-717.
12. Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531, and references cited therein.
13. Introduction of a 3-hydroxypropyl group, via the 7-endo-radical cyclization with a temporary-connecting allylsilyl-tether followed by Tamao oxidation, has been reported: (a) Xi, Z.; Agback, P.; Plavec, J.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1992, 48, 349-370.
14. (b) Kanazaki, M.; Ueno, Y.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 2000, 122, 2422-2432.
15. Intermolecular reactions to anomeric radicals of glucose derivatives selectively occur from the axial direction due to the anomeric effect to give the corresponding α-products: Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969-980.
16. 4-form, in which the bulky substituents are in axial positions due to mutual steric repulsion: (a) Hosoya, T.; Ohashi, Y.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1996, 37, 663-666.
17. (b) Walford, C.; Jackson, R. F. W.; Rees, N. H.; Clegg, W.; Heath, S. L. J. Chem. Soc., Chem. Commun. 1997, 1855-1856.
18. (c) Roush, W. R.; Sebesta, S. P.; Bennett, C. E. Tetrahedron 1997, 53, 8825-8836.
19. (d) Ichikawa, S.; Shuto, S.; Matsuda, A. J. Am. Chem. Soc. 1999, 121, 10270-10280.
20. Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2122-2124.
21. Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054-7055.
22. Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656-6660.
23. The reactivity of the phenylseleno group at the 1β-positon of 7 may be decreased due to significant 1,3-diaxial repulsion.