Asymmetric strecker synthesis of C-glycopeptide

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4440-4443

  Vincent, Stéphane P ^a   Schleyer, Axel ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOPEPTIDE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS;

CARBOHYDRATE CONFORMATION; GLYCOPEPTIDES; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MONOSACCHARIDES;

EID: 0034647745     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000034p     Document Type: Article

References (37)

1. For a recent review, see: Marcaurelle, L.; Bertozzi, C. R. Chem. Eur. J. 1999, 5, 1384-1390.
2. Kihlberg, J.; Elofsson, M. Curr. Med. Chem. 1997, 4, 85-116.
3. Kuduk, S. D.; Schwarz, a. B.; Chen, X.-T.; Glunz, P. W.; Sames, D.; Ragupathi, G.; Livingston, P. O.; Danishefsky, S. J. J. Am. Chem. Soc. 1998, 120, 12474-12485.
4. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
5. Herpin, T.; Motherwell, W.; Weibel, J.-M. Chem. Commun. 1997, 923.
6. Burkhart, F.; Hoffman, M.; Kesler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192.
7. Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094.
8. Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956.
9. Pearce, A. J.; Ramaya, S.; Thorn, S. N.; Bloomberg, G. B.; Walter, D. S.; Gallager, T. J. Org. Chem. 1999, 64, 5453-5462.
10. Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898.
11. Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470.
12. Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820.
13. Wong, C.-H.; Moris-Varas, F.; Lin, C.-C.; Gong, K. W.; Weitz-Schmidt, G. J. Am. Chem. Soc. 1997, 119, 8152-8158.
14. Lampe, T. F. J.; Weitz-Schmidt, G.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 97, 1707-1711.
15. Simanek, E. E.; McGarvey, G. J.; Jablonowski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833-862.
16. Dondoni, A.; Massi, A.; Marra, A. Tetrahedron Lett. 1998, 39, 6601-6604.
17. Kessler, H.; Wittman, V.; Kock, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904.
18. Kishi, Y. Pure Appl. Chem. 1989, 61, 313-324.
19. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
20. Weltering, T. J.; Weitz-Schmidt, G.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 9033-9036.
21. Uchiyama, T.; Woltering, T. J.; Wong, W.; Lin, C.-C.; Kajimoto, T.; Takebayashi, M.; Weitz-Scmidt, G.; Asakura, T.; Noda, M.; Wong, C.-H. Bioorg. Med. Chem. 1996, 4, 1149-1165.
22. Marron, T. G.; Woltering, T. J.; Weitz-Scmidt, G.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 9037-9040.
23. Tsai, C.-Y.; Park, W.; Weitz-Schmidt, G.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1998, 8, 2333-2338.
24. Jacques, F.; Dupeyroux, H.; Joly, J.-P.; Chapleur, Y. Tetrahedron Lett. 1997, 38, 73-76.
25. Arya, P.; Ben, R. N.; Qin, H. Tetrahedron Lett. 1998, 39, 6131-6134.
26. Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1991, 56, 4326-4329.
27. Panek, J. S.; Sparks, M. A. J. Org. Chem. 1989, 54, 2034-2038.
28. Sutherlin, D. P.; Spark, T. M.; Hugues, E.; Armstrong, R. W. J. Org. Chem. 1996, 61, 8350-8354.
29. Kunz, H.; Sager, W.; Schanzenbach, D.; Decker, M. Liebigs Ann. Chem. 1991, 649-54.
30. Kunz, H.; Sager, W.; Pfrengle, W.; Laschat, S.; Schanzenbach, D. Chem. Pept. Proteins 1993, 5/6, 91-8.
31. Duthaler, R. O. Tetrahedron 1994, 50, 1539-650.
32. Stout, D. M.; Black, L. A.; Matier, W. L. J. Org. Chem. 1983, 48, 5369-5373.
33. Inaba, T.; Fujita, M.; Ogura, K. J. Org. Chem. 1991, 56, 1274-1279.
34. In all cases, in THF with (S)-(-)-α-methylbenzylamine 1, the protons vicinal to the nitrile of the major isomer were always upfield, compared to the minor isomer, in the NMR spectra. The (S) stereochemistry was therefore assigned to the major isomer.
35. Bloch, R. Chem. Rev. 1998, 98, 1407-1438.
36. Speelman, J. C.; Talma, A. G.; Kellogg, R. M.; Meetsma, A.; Boer, J. L. d.; Beurskens, P. T.; Bosman, W. P. J. Org. Chem. 1989, 54, 1055-1062.
37. This type of solvent dependent reversal of induction has a few precedents in the literature. For references, see: Kunz, H.; Sager, W.; Pflenle, W.; Schanzenbach, D. Tetrahedron Lett. 1988, 29, 4397-4400.