Armed/Disarmed Effects in Glycosyl Donors: Rationalization and Sidetracking

Journal of Organic Chemistry

Volumn 55, Issue 25, 1990, Pages 6068-6070

  Fraser Reid, Bert ^a   Wu, Zufan ^a   Udodong, Uko E ^a   Ottosson, Hakan ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 12444311462     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00312a004     Document Type: Article

References (21)

1. The terms “armed” and “disarmed” are used3 instead of activated and deactivated since a disarmed donor can, in fact, be readily activated.
2. Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583.
3. Mootoo, D. R.; Date, V.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 2662.
4. This work was supported grants from the National Science Foundation (CHE 8920033), the National Institutes of Health (GM 41071), and Glycomed, Hayward, CA.
5. Friesen, R. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6656.
6. Mereyala, H. N.; Reddy, G. V. 17th IUPAC International Symposium on the Chemistry of Natural Products, New Delhi, India, February 49, 1990.
7. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
8. Veeneman, G. H.; Van Boom, J. H. Tetrahedron Lett. 1990, 31, 275.
9. Feather, M. S.; Harris, J. F. J. Org. Chem. 1965, 30,153.
10. BeMiller, J. N.; Doyle, E. R. Carbohydr. Res. 1971, 20, 23.
11. Cocker, D.; Sinnott, M. L. J. Chem. Soc., Perkin Trans. 2 1976, 618.
12. Fraser-Reid, B.; Boctor, B. Can. J. Chem. 1969, 47, 393.
13. Buncell, E.; Bradley, P. R. Can. J. Chem. 1967, 45, 515.
14. Overend, W. G.; Rees, C. W.; Sequeira, J. S. J. Chem. Soc. 1962, 3429.
15. For discussion of a comparable process see: Bochkov, A. F.,; Zaikov, G. E. Chemistry of the O-Glycosidic Bond: Formation and Cleavage; Pergamon Press: New York, 1979,
16. Igarishi, K. Adv. Carbohydr. Chem. Biochem. 1977, 34, 243.
17. The rationalization presented in Figure 1 can be adapted to the observations made by Friesen and Danishefsky on glycal donors5 as shown below.
18. Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1990, 270.
19. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
20. Konradsson, P.; Fraser-Reid, B. J. Chem. Soc.,Chem. Commun. 1989, 1124.
21. Since this preliminary report on our early work, additional experiments have revealed the formation of vicinal dibromides (16) in attempts to prepare glycosyl bromides (19) but only when Y = ester.