Investigations towards the synthesis of dTDP-2,6-dideoxy-D-erythro-3-hexulose - A potential intermediate in the biosynthesis of rare sugars

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5473-5476

  Müller, Thomas ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYSUGAR;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 17144459830     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01224-0     Document Type: Article

References (42)

1. This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.
2. Griesebach, H. Adv. Carbohydr. Chem. Biochem. 1978, 35, 81-126; Shibaev, V.N. ibid. 1986, 44, 277-339.
3. Griesebach, H. Adv. Carbohydr. Chem. Biochem. 1978, 35, 81-126; Shibaev, V.N. ibid. 1986, 44, 277-339.
4. Thorson, J.S., Lo, S.F., Liu, H.-W., Hutchinson, C.R. J. Am. Chem. Soc. 1993, 115, 6993-6994; Liu, H.-W. Thorson, J.S. Annu. Rev. Microbiol. 1994, 48, 223-256, zit. Lit.
5. Thorson, J.S., Lo, S.F., Liu, H.-W., Hutchinson, C.R. J. Am. Chem. Soc. 1993, 115, 6993-6994; Liu, H.-W. Thorson, J.S. Annu. Rev. Microbiol. 1994, 48, 223-256, zit. Lit.
6. Okazaki, R., Okazaki, T., Strominger, J.L., Michelson, A.M. J. Biol. Chem. 1962, 237, 3014-3026; Snipes, C.E., Brillinger, G.U., Sellers, L., Mascaro, L., Floss, H.G. ibid. 1977, 252, 8113-8117.
7. Okazaki, R., Okazaki, T., Strominger, J.L., Michelson, A.M. J. Biol. Chem. 1962, 237, 3014-3026; Snipes, C.E., Brillinger, G.U., Sellers, L., Mascaro, L., Floss, H.G. ibid. 1977, 252, 8113-8117.
8. Stein, A., Kula, M.-R., Elling, L., Verseck, S., Klaffke, W. Angew. Chem. 1995, 107, 1881-1883; Angew. Chem. Int. Ed. Engl. 1995, 34, 1741-1743.
9. Stein, A., Kula, M.-R., Elling, L., Verseck, S., Klaffke, W. Angew. Chem. 1995, 107, 1881-1883; Angew. Chem. Int. Ed. Engl. 1995, 34, 1741-1743.
10. Snipes, C.E., Chang, C., Floss, H.G. J. Am. Chem. Soc. 1979, 101, 701-706; Floss, H.G. in The Antibiotics, Vol. 4 (Hrsg.: Corcoran, J.W.), Springer, Berlin, 1981, S. 215-235; Lee, J.J., Lee, J.P., Keller, P.J., Cottrell, C.E., Chang, C.-J. J. Antibiotics 1986, 39, 1123-1134.
11. Snipes, C.E., Chang, C., Floss, H.G. J. Am. Chem. Soc. 1979, 101, 701-706; Floss, H.G. in The Antibiotics, Vol. 4 (Hrsg.: Corcoran, J.W.), Springer, Berlin, 1981, S. 215-235; Lee, J.J., Lee, J.P., Keller, P.J., Cottrell, C.E., Chang, C.-J. J. Antibiotics 1986, 39, 1123-1134.
12. Snipes, C.E., Chang, C., Floss, H.G. J. Am. Chem. Soc. 1979, 101, 701-706; Floss, H.G. in The Antibiotics, Vol. 4 (Hrsg.: Corcoran, J.W.), Springer, Berlin, 1981, S. 215-235; Lee, J.J., Lee, J.P., Keller, P.J., Cottrell, C.E., Chang, C.-J. J. Antibiotics 1986, 39, 1123-1134.
13. Heinz, E., Schmidt, H., Hoch, M., Jung, K.-H., Schmidt, R.R. Eur. J. Biochem. 1989, 184, 445-453; Hoch, M., Heinz, E., Schmidt, R.R. Carbohydr. Res. 1989, 193, 33-47; Schmidt, R.R., Wegmann, B., Jung, K.-H. Liebigs Ann. Chem. 1991, 121-124.
14. Heinz, E., Schmidt, H., Hoch, M., Jung, K.-H., Schmidt, R.R. Eur. J. Biochem. 1989, 184, 445-453; Hoch, M., Heinz, E., Schmidt, R.R. Carbohydr. Res. 1989, 193, 33-47; Schmidt, R.R., Wegmann, B., Jung, K.-H. Liebigs Ann. Chem. 1991, 121-124.
15. Heinz, E., Schmidt, H., Hoch, M., Jung, K.-H., Schmidt, R.R. Eur. J. Biochem. 1989, 184, 445-453; Hoch, M., Heinz, E., Schmidt, R.R. Carbohydr. Res. 1989, 193, 33-47; Schmidt, R.R., Wegmann, B., Jung, K.-H. Liebigs Ann. Chem. 1991, 121-124.
16. Eisele, T., Schmidt, R.R. unpublished; Eisele, T. Diplomarbeit, Universität Konstanz, 1993.
17. Eisele, T., Schmidt, R.R. unpublished; Eisele, T. Diplomarbeit, Universität Konstanz, 1993.
18. Müller, T., Schmidt, R.R. Angew. Chem. 1995, 107, 1467-1468; Angew. Chem. Int. Ed. Engl. 1995, 34, 1328-1329.
19. Müller, T., Schmidt, R.R. Angew. Chem. 1995, 107, 1467-1468; Angew. Chem. Int. Ed. Engl. 1995, 34, 1328-1329.
20. Müller, T., Schmidt, R.R. Liebigs Ann. Chem., submitted.
21. Hadfield, A.F., Sartorelli, A.C. Carbohydr. Res. 1982, 101, 197-208; Sabesan, S. Neira, S. J. Org. Chem. 1991, 56, 5468-5472.
22. Hadfield, A.F., Sartorelli, A.C. Carbohydr. Res. 1982, 101, 197-208; Sabesan, S. Neira, S. J. Org. Chem. 1991, 56, 5468-5472.
23. Zemplén, G. Ber. Dtsch. Chem. Ges. 1927, 60, 1555-1564.
24. Müller, T., Schneider, R., Schmidt, R.R. Tetrahedron Lett. 1994, 35, 4763-4766; Schneider, R., Diplomarbeit, Universität Konstanz, 1994.
25. Müller, T., Schneider, R., Schmidt, R.R. Tetrahedron Lett. 1994, 35, 4763-4766; Schneider, R., Diplomarbeit, Universität Konstanz, 1994.
26. Hanessian, S. Carbohydr. Res. 1966, 2, 86-88; Adv. Carbohydr. Chem. 1966, 21, 143-207; Hanessian, S., Plessas, N.R. J. Org. Chem. 1969, 34, 1035-1044.
27. Hanessian, S. Carbohydr. Res. 1966, 2, 86-88; Adv. Carbohydr. Chem. 1966, 21, 143-207; Hanessian, S., Plessas, N.R. J. Org. Chem. 1969, 34, 1035-1044.
28. Hanessian, S. Carbohydr. Res. 1966, 2, 86-88; Adv. Carbohydr. Chem. 1966, 21, 143-207; Hanessian, S., Plessas, N.R. J. Org. Chem. 1969, 34, 1035-1044.
29. Tebbe, F.N., Parshall, G.W., Reddy, G.S. J. Am. Chem. Soc. 1978, 100, 3611-3613; Camizzo, L.F., Grubbs, R-H. J. Org. Chem. 1985, 50, 2387-2390; Pine, S.H. Org. React. 1993, 43, 1-16.
30. Tebbe, F.N., Parshall, G.W., Reddy, G.S. J. Am. Chem. Soc. 1978, 100, 3611-3613; Camizzo, L.F., Grubbs, R-H. J. Org. Chem. 1985, 50, 2387-2390; Pine, S.H. Org. React. 1993, 43, 1-16.
31. Tebbe, F.N., Parshall, G.W., Reddy, G.S. J. Am. Chem. Soc. 1978, 100, 3611-3613; Camizzo, L.F., Grubbs, R-H. J. Org. Chem. 1985, 50, 2387-2390; Pine, S.H. Org. React. 1993, 43, 1-16.
32. +]-.
33. Brimacombe, J.S., Da'Aboul, I., Tucker, L.C.N. Carbohydr. Res. 1971, 19, 276-280; Fraser-Reid, B., Kelly, D.R., Tulshian, D.B., Ravi, P.S. J. Carbohydr. Chem. 1983, 2, 105-114.
34. Brimacombe, J.S., Da'Aboul, I., Tucker, L.C.N. Carbohydr. Res. 1971, 19, 276-280; Fraser-Reid, B., Kelly, D.R., Tulshian, D.B., Ravi, P.S. J. Carbohydr. Chem. 1983, 2, 105-114.
35. Kinzy, W., Schmidt, R.R. Tetrahedron Lett. 1987, 28, 1981-1984.
36. Martin, T.J., Schmidt, R.R. Tetrahedron Lett. 1992, 33, 6123-6126; Martin, T.J., Brescello, R., Toepfer, A., Schmidt, R.R. Glycoconjugate J. 1993, 10, 16-25.
37. Martin, T.J., Schmidt, R.R. Tetrahedron Lett. 1992, 33, 6123-6126; Martin, T.J., Brescello, R., Toepfer, A., Schmidt, R.R. Glycoconjugate J. 1993, 10, 16-25.
38. Müller, T., Dissertation, Universität Konstanz, 1996.
39. Schmidt, R.R., Frische, K. Bioorg. Med. Chem. Lett. 1993, 3, 1747-1750; Frische, K., Schmidt, R.R. Liebigs Ann. Chem. 1994, 297-303.
40. Schmidt, R.R., Frische, K. Bioorg. Med. Chem. Lett. 1993, 3, 1747-1750; Frische, K., Schmidt, R.R. Liebigs Ann. Chem. 1994, 297-303.
41. Roseman, S., Distler, J.J., Moffat, J.G., Khorana, H.G. J. Am Chem. Soc. 1961, 83, 659-663; Moffat, J.G. Methods Enzymol. 1966, 8, 136-142.
42. Roseman, S., Distler, J.J., Moffat, J.G., Khorana, H.G. J. Am Chem. Soc. 1961, 83, 659-663; Moffat, J.G. Methods Enzymol. 1966, 8, 136-142.