Selectively deprotectable carbohydrates based on regioselective enzymatic reactions

Synlett

Volumn , Issue 11, 1999, Pages 1817-1819

  Pfau, Roland ^a   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Carbohydrates; Enzymes; Isobutyryl group; Protecting groups; Regioselectivity

Indexed keywords

2 AZIDO 2 DEOXYGALACTOPYRANOSIDE; CARBOHYDRATE DERIVATIVE; GALACTAL; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEACYLATION; ENZYME ACTIVITY; STEREOCHEMISTRY;

EID: 0032753190     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2928     Document Type: Article

References (25)

1. Reviews: a) Kocienski, P. J. Protecting Groups, Georg Thieme Verlag, Stuttgart, New York 1994;
2. b) Kunz, H.; Waldmann, H. in Comprehensive Organic Synthesis (Trost, B. M.; Fleming, I. Eds.) Vol. VI, Pergamon Press, Oxford, 1991, p. 631.
3. Bols, M. Carbohydrate Building Blocks, Wiley-Interscience, New York 1996.
4. a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem. 1998, 110, 2620; Angew. Chem. Int. Ed. Engl. 1998, 37, 2503;
5. a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem. 1998, 110, 2620; Angew. Chem. Int. Ed. Engl. 1998, 37, 2503;
6. b) Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7130.
7. Review: Reidel, A.; Waldmann, H. J. Prakt. Chem. 1993, 335, 109.
8. Eberling, J.; Braun, P.; Kowalczyk, D.; Schultz, M.; Kunz, H. J. Org. Chem. 1996, 61, 2638.
9. Drueckhammer, D. G.; Hennen, W. J.; Pederson, R. L.; Barbas, C. F.; Gautheron, C. M.; Krach, T.; Wong, C.-H. Synthesis 1991, 499.
10. Hennen, W. J.; Sweers, H. M.; Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 4939.
11. Holla, E. W. Angew. Chem. 1989, 101, 222; Angew. Chem. Int. Ed. Engl. 1989, 28, 220.
12. Holla, E. W. Angew. Chem. 1989, 101, 222; Angew. Chem. Int. Ed. Engl. 1989, 28, 220.
13. Waldmann, H.; Heuser, A.; Reidel, A. Synlett 1994, 1, 65.
14. a) Kindly donated by Amano Enzyme Ltd., Witan Court, 297 Upper Fourth Street, Milton Keynes, MK9 1EH, U.K.
15. b) Purchased from Sigma, Sigma-Adrich Chemie GmbH, D-82039 Deisenhofen, Germany.
16. Palomaa, M. H.; Siilonen, T. A. Chem. Ber. 1930, 63, 3117.
17. Kunz, H.; Kowalczyk, D.; Braun, P.; Braum, G. Angew. Chem. 1994, (12)106, 393; Angew. Chem. Int. Ed. Engl. 1994, 33, 336.
18. Kunz, H.; Kowalczyk, D.; Braun, P.; Braum, G. Angew. Chem. 1994, (12)106, 393; Angew. Chem. Int. Ed. Engl. 1994, 33, 336.
19. Rilling, P.; Walter, T.; Pommersheim, R.; Vogt, W. J. Membr. Sci. 1997, 129, 283.
20. Reetz, M. T. Adv. Mater. 1997, 9, 943.
21. Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 3127; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393.
22. Wang, Y.-F.; Wong, C.-H. J. Org. Chem. 1988, 53, 3127; Fang, J.-M.; Wong, C.-H. Synlett 1994, 393.
23. Guibé, F.; Saint M'Leux, Y. Tetrahedron Lett. 1981, 22, 3591.
24. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482; Angew. Chem. Int. Ed. Engl. 1996, 108, 1380.
25. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem. 1996, 108, 1482; Angew. Chem. Int. Ed. Engl. 1996, 108, 1380.