The Grignard reagent from 2-bromomethyl-1,3-dioxolane, a novel and efficient d2-reagent: Synthesis of branched chain carbohydrate derivatives

Synthesis

Volumn , Issue 8, 1996, Pages 1002-1006

  Schmeichel, Martina ^a   Redlich, Hartmut ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

2 bromomethyl 1,3 dioxolane; carbohydrate ketones; d2 synthon; Grignard reagent; magnesium

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029834218     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4321     Document Type: Article

References (24)

1. Stowell, J. C. Chem. Rev. 1984, 84, 409.
2. Newman, H. Tetrahedron 1971, 4571.
3. Benkeser, R. A. Synthesis 1971, 347.
4. Bailey, P. S. Ozonation in Organic Chemistry, Vol. 1: Olefinic Compounds, Academic: New York, 1978.
5. Seyferth, D.; Mueller, D. C.; Armbrecht, Jr., F. M. Organometallics in Chemical Synthesis 1970/71, 1 (3), 127. Villiéras, J.; Bacquet, C.; Normant, J.-F. Bull. Soc. Chim. Fr. 1974, 1731.
6. Seyferth, D.; Mueller, D. C.; Armbrecht, Jr., F. M. Organometallics in Chemical Synthesis 1970/71, 1 (3), 127. Villiéras, J.; Bacquet, C.; Normant, J.-F. Bull. Soc. Chim. Fr. 1974, 1731.
7. Barluenga, J.; Fañarás, J. F.; Yus, M. J. Org. Chem. 1979, 44, 4798.
8. Seebach, D.; Hungerbühler, E. Modern Synthetic Methods, Vol. 2, Otto Salle Verlag: Frankfurt a. Main Berlin München, 1980, pp 91.
9. Büchi, G.; Wüest, H. J. Org. Chem. 1969, 34, 1122.
10. Feugeas, C. Bull. Soc. Chim. Fr. 1963, 2568.
11. Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1986, 51 (22), 4245.
12. Yoshimura, J.; Sato, K.; Hashimoto, H. Chem. Lett. 1977, 1327. Herscovici, J.; Antonakis, K. J. Chem. Soc. Chem. Commun. 1980, 561.
13. Yoshimura, J.; Sato, K.; Hashimoto, H. Chem. Lett. 1977, 1327. Herscovici, J.; Antonakis, K. J. Chem. Soc. Chem. Commun. 1980, 561.
14. Wakefield, B. J. Organomagnesium Methods in Organic Synthesis, Academic: London San Diego New York, 1995, p 32.
15. Using small amounts of ketones it was easier to work with 5-10 equiv of Grignard reagent 3.
16. Pohmakotr, M.; Geiss, K.-H.; Seebach, D. Chem. Ber. 1979, 112, 1420.
17. Assignment of configuration was achieved by NOE experiments: saturating 1′-H: 1-H 2.3%, saturating benzylidene-H: dioxolane-H 3.6%, compound 11; saturating 2′a-H and 2′b-H: 4-H 5%, compound 12; saturating H-6e: dioxolane-H 1.2%, compound 14.
18. Yoshimura, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69.
19. Garegg, P. J.; Iversen, T.; Oscarson, S. Carbohydr. Res. 1976, 50, C12. Lee, E. E.; Keaveney, G.; O'Colla, P. S. Carbohydr. Res. 1977, 59, 268.
20. Garegg, P. J.; Iversen, T.; Oscarson, S. Carbohydr. Res. 1976, 50, C12. Lee, E. E.; Keaveney, G.; O'Colla, P. S. Carbohydr. Res. 1977, 59, 268.
21. Rosenthal, A.; Catsoulacos, P. Can. J. Chem. 1969, 47, 2747.
22. Horton, D.; Nakadate, M.; Tronchet, J. M. J. Carbohydr. Res. 1968, 7, 56.
23. 5,6 = 5.4 Hz; Lemieux, R. U.; Martin, C. J. Carbohydr. Res. 1970, 13, 139; Paulsen, H.; Redlich, H. Chem. Ber. 1974, 107, 2992.
24. 5,6 = 5.4 Hz; Lemieux, R. U.; Martin, C. J. Carbohydr. Res. 1970, 13, 139; Paulsen, H.; Redlich, H. Chem. Ber. 1974, 107, 2992.