New factors governing stereoselectivity in borohydride reductions of β-D-glycoside-2-uloses - The peculiar effect of "activated" DMSO

European Journal of Organic Chemistry

Volumn , Issue 23, 2000, Pages 3931-3935

  Kerékgyártó, János ^a   Rákó, János ^a   Ágoston, Károly ^a   Gyémánt, Gyöngyi ^a   Szurmai, Zoltán ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Asymmetric synthesis; Carbohydrates; Epimerization; Reductions; D Mmannosides

Indexed keywords

GLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; MOLECULAR DYNAMICS; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033675189     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200012)2000:23<3931::AID-EJOC3931>3.0.CO;2-W     Document Type: Article

References (20)

1. H. Paulsen, Angew. Chem. Int. Ed. Engl. 1982, 21, 155-173.
2. [2a] E. Kaji, F. W. Lichtenthaler, Trends Glycosci. Glycotech. 1993, 5, 121-142.
3. [2b] F. Barresi, O. Hindsgaul in Modern Methods in Carbohydrate Synthesis (Eds.: S. H. Kahn, R. O. O'Neill), Harwood, Amsterdam, 1996, chapter 11.
4. [2c] G. Arsequell, G. Valencia, Tetrahedron: Asymmetry 1999, 10, 3045-3094.
5. [3a] G. Ekborg, B. Lindberg, J. Lönngren, Acta Chem. Scand. 1972, 26, 3287-3292.
6. [3b] M. A. E. Shaban, R. W. Jeanloz, Carbohydr. Res. 1976, 52, 103-114,
7. Carbohydr. Res. 1976, 52, 115-127.
8. [3c] C. D. Waren, C. Augé, M. L. Laver, S. Suzuki, D. Power, R. W. Jeanloz, Carbohydr. Res. 1980, 82, 71-83.
9. [3d] J. Kerékgyártó, J. P. Kamerling, J. B. Bouwstra, J. F. G. Vliegenthart, A. Lipták, Carbohydr. Res. 1989, 186, 51-62.
10. [3e] J. Kerékgyártó, J. G. M. van der Ven, J. P. Kamerling, A. Lipták, J. F. G. Vliegenthart, Carbohydr. Res. 1993, 238, 135-145.
11. [3f] J. Kerékgyártó, K. Agoston, Gy. Batta, J. P. Kamerling, J. F. G. Vliegenthart, Tetrahedron Lett. 1998, 39, 7189-7192.
12. [4a] F. W. Lichtenthaler, U. Kläres, M. Lergenmüller, S. Schwidetzky, Synthesis 1992, 179-184.
13. [4b] F. W. Lichtenthaler, T. Schneider-Adams, J. Org. Chem. 1994, 59, 6728-6734.
14. [4c] A. Fürstner, I. Konetzki, Tetrahedron 1996, 52, 15071-15078.
15. [4d] F. W. Lichtenthaler, U. Kläres, Z. Szurmai, B. Werner, Carbohydr. Res. 1998, 305, 293-303.
16. J. E. T. Corril, J. Chem. Soc., Perkin Trans. 1 1993, 2161-2166.
17. P. A. Finan, C. D. Warren, J. Chem. Soc. 1962, 3089-3092.
18. M. T. Barros, C. D. Maycock, M. R. Ventura, Tetrahedron Lett. 1999, 40, 557-560.
19. A. J. Mancuso, D. Swern, Synthesis 1981, 165-196.
20. J. G. M. van der Ven, J. Kerékgyártó, J. P. Kamerling, A. Lipták, J. F. G. Vliegenthart, Carbohydr. Res. 1994, 264, 45-62.