Synthesis of C-Linked Glycosyl Amino Acid Derivatives using Organozinc Reagents

Synlett

Volumn 1996, Issue 9, 1996, Pages 859-861

  Dorgan, Brian J ^a   Jackson, Richard F W ^a  

^a Bedson Building ^*  (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542710321     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5599     Document Type: Article

References (22)

1. Petrus, L.; BeMiller, J.N. Carbohydr. Res. 1992, 230, 197-200; Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904; Bertozzi, C.R.; Hoeprich, P.D., Jr.; Bednarski, M.D. J. Org. Chem. 1992, 57, 6092-6094; Bertozzi, C.R.; Cook, D.G.; Kobertz, W.R.; Gonzalez-Scarano, F.; Bednarski, M.D. J. Am. Chem. Soc. 1992, 114, 10639-10641; Gurjar, M.K.; Mainkar, A.S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343-2346; Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
2. Petrus, L.; BeMiller, J.N. Carbohydr. Res. 1992, 230, 197-200; Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904; Bertozzi, C.R.; Hoeprich, P.D., Jr.; Bednarski, M.D. J. Org. Chem. 1992, 57, 6092-6094; Bertozzi, C.R.; Cook, D.G.; Kobertz, W.R.; Gonzalez-Scarano, F.; Bednarski, M.D. J. Am. Chem. Soc. 1992, 114, 10639-10641; Gurjar, M.K.; Mainkar, A.S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343-2346; Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
3. Petrus, L.; BeMiller, J.N. Carbohydr. Res. 1992, 230, 197-200; Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904; Bertozzi, C.R.; Hoeprich, P.D., Jr.; Bednarski, M.D. J. Org. Chem. 1992, 57, 6092-6094; Bertozzi, C.R.; Cook, D.G.; Kobertz, W.R.; Gonzalez-Scarano, F.; Bednarski, M.D. J. Am. Chem. Soc. 1992, 114, 10639-10641; Gurjar, M.K.; Mainkar, A.S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343-2346; Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
4. Petrus, L.; BeMiller, J.N. Carbohydr. Res. 1992, 230, 197-200; Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904; Bertozzi, C.R.; Hoeprich, P.D., Jr.; Bednarski, M.D. J. Org. Chem. 1992, 57, 6092-6094; Bertozzi, C.R.; Cook, D.G.; Kobertz, W.R.; Gonzalez-Scarano, F.; Bednarski, M.D. J. Am. Chem. Soc. 1992, 114, 10639-10641; Gurjar, M.K.; Mainkar, A.S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343-2346; Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
5. Petrus, L.; BeMiller, J.N. Carbohydr. Res. 1992, 230, 197-200; Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904; Bertozzi, C.R.; Hoeprich, P.D., Jr.; Bednarski, M.D. J. Org. Chem. 1992, 57, 6092-6094; Bertozzi, C.R.; Cook, D.G.; Kobertz, W.R.; Gonzalez-Scarano, F.; Bednarski, M.D. J. Am. Chem. Soc. 1992, 114, 10639-10641; Gurjar, M.K.; Mainkar, A.S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343-2346; Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
6. Petrus, L.; BeMiller, J.N. Carbohydr. Res. 1992, 230, 197-200; Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904; Bertozzi, C.R.; Hoeprich, P.D., Jr.; Bednarski, M.D. J. Org. Chem. 1992, 57, 6092-6094; Bertozzi, C.R.; Cook, D.G.; Kobertz, W.R.; Gonzalez-Scarano, F.; Bednarski, M.D. J. Am. Chem. Soc. 1992, 114, 10639-10641; Gurjar, M.K.; Mainkar, A.S.; Syamala, M. Tetrahedron: Asymmetry 1993, 4, 2343-2346; Axon, J.R.; Beckwith, A.L.J. J. Chem. Soc., Chem. Commun. 1995, 549-550.
7. Jackson, R.F.W.; Wishart, N.; Wood, A.; James, K.; Wythes, M.J. J. Org. Chem., 1992, 57, 3397-3404.
8. Dunn, M.J.; Jackson, R.F.W.; Pietruszka, J.; Turner, D. J. Org. Chem. 1995, 60, 2210-2215.
9. Fraser, J.L.; Jackson, R.F.W.; Porter, B. Synlett 1994, 379-380; Fraser, J.L.; Jackson, R.F.W.; Porter, B. Synlett 1995, 819-820.
10. Fraser, J.L.; Jackson, R.F.W.; Porter, B. Synlett 1994, 379-380; Fraser, J.L.; Jackson, R.F.W.; Porter, B. Synlett 1995, 819-820.
11. Fraser, J.L.; Jackson, R.F.W.; Porter, B. unpublished observations.
12. Pirrung, M.C.; Lee, Y.R. J. Chem. Soc., Chem. Commun. 1995, 673-674.
13. For the selective 4,6-protection of glucose derivatives, see: van Boeckel, C.A.A.; van Boom, J.H. Tetrahedron 1985, 41 4545-4555. See also: Markiewicz, W.T. J. Chem. Res. (S) 1979, 24-25.
14. For the selective 4,6-protection of glucose derivatives, see: van Boeckel, C.A.A.; van Boom, J.H. Tetrahedron 1985, 41 4545-4555. See also: Markiewicz, W.T. J. Chem. Res. (S) 1979, 24-25.
15. Ogihara, T.; Mitsunobu, O. Tetrahedron Lett. 1983, 24, 3505-3508.
16. The stereochemistry of the glycoside 8 was established by nOe experiments on the compound derived by hydrogenation and removal of the silyl protection.
17. 4), filtered and the solvent evaporated. Column chromatography using petroleum ether-ethyl acetate (9:1) as eluant gave the 3-substituted product 10 (219 mg, 49 %) and the 1-substituted product 11 (72 mg, 16 %)
18. 2Me
19. Mitsunobu, O.; Yoshida, M.; Takiya, M.; Kubo, K.; Maruyama, S.; Satoh, I.; Iwami, H. Chem. Lett. 1989, 809-812.
20. Thorn, S.N.; Gallagher, T. Synlett 1996, 856.
21. Thorn, S.N.; Gallagher, T. Synlett 1996, 185-187.
22. The stereochemistry of compound 23 was established by the triplet exhibited by the proton at C-4, indicating a trans-relationship between this proton and the proton at C-3 (since the protons at C-4 and C-5 are necessarily trans).