Activation of glycosyl phosphates by in situ conversion to glycosyl iodides under neutral conditions in concentrated solutions of lithium perchlorate in organic solvents

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3837-3840

  Schmid, Uschi ^a   Waldmann, Herbert ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; GLYCOSYL IODIDE; GLYCOSYL PHOSPHATE; LITHIUM DERIVATIVE; LITHIUM PERCHLORATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; GLYCOSYLATION; IODINATION; REACTION ANALYSIS;

EID: 0029891239     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00729-0     Document Type: Article

References (28)

1. Reviews: a) L. A. Lasky, Science 1992, 258, 964;
2. b) S. Hakomori, Adv. Cancer Res. 1989, 52, 257;
3. c) T. Feizi, Nature 1985, 314, 53;
4. d) J. C. Paulson in The Receptors, Vol. 2 (M. Conn, ed.), Academic Press, New York, 1985, p. 131;
5. e) A. Varki, Glycobiology 1993, 3, 97.
6. Rewies on glycoside synthesis: a) H. Paulsen, Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155;
7. Rewies on glycoside synthesis: a) H. Paulsen, Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155;
8. b) R. R. Schmidt, Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212;
9. b) R. R. Schmidt, Angew. Chem. 1986, 98, 213; Angew. Chem. Int. Ed. Engl. 1986, 25, 212;
10. c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503;
11. d) C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453 and 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
12. d) C.-H. Wong, R. L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453 and 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 412.
13. Review on the relevance of oligosaccharides to medicinal chemistry: J. H. Musser, Ann. Rep. Med. Chem. 1992, 27, 301.
14. J. Thiem, S. Köpper, J. Carbohydr. Chem. 1983, 2, 75.
15. F. J. Kronzer, C. Schuerch, Carbohydr. Res. 1974, 34, 71.
16. See: O. Lockhoff in: Methoden Org. Chem. (Houben-Weyl), 4th Ed., Thieme, Stuttgart 1992, Vol. E 14a/3, pp. 724-729.
17. A. Klemer, M. Bieber, Liebigs Ann. Chem. 1984, 1052.
18. a) E. Fischer, H. Fischer, Ber. 1910, 43, 2535;
19. b) D. H. Braun, J. Am. Chem. Soc. 1924, 46, 1484;
20. c) R. K. Ness, H. G. Fletcher jr., C. S. Hudson, J. Am. Chem. Soc. 1950, 72, 2200;
21. d) R. U. Lemieux, T. Takeda, B. Y. Chung, ACS Symp. Ser. 1976, 39, 90.
22. R. R. Schmidt in Carbohydrates - Synthetic Methods and Applications in Medicinal Chemistry (Eds.: H. Ogura, A. Hasegewa, T. Suami), VCH, Weinheim, 1992, chapter 4, pp. 66-88.
23. a) H. Waldmann, G. Böhm, U. Schmid, H. Röttele, Angew. Chem. 1994, 106, 2024; Angew. Chem. Int. Ed. Engl. 1994, 33, 1944;
24. a) H. Waldmann, G. Böhm, U. Schmid, H. Röttele, Angew. Chem. 1994, 106, 2024; Angew. Chem. Int. Ed. Engl. 1994, 33, 1944;
25. b) G. Böhm, H. Waldmann, Tetrahedron Lett. 1995, 36, 3843;
26. c) G. Böhm, H. Waldmann, Liebigs Ann. Chem. 1996, 613 and 621.
27. +.
28. R. R. Schmidt, M. Behrendt, A. Toepfer, Synlett 1990, 694.