Practical stereoselective synthesis of α-D-C-mannosyl-(R)-alanine

Tetrahedron

Volumn 58, Issue 46, 2002, Pages 9381-9386

  Colombo, Lino ^a   Di Giacomo, Marcello ^a   Ciceri, Paola ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

C glycosyl amino acids; Claisen rearrangement; Quaternary amino acids

Indexed keywords

ALANINE DERIVATIVE; ALPHA DEXTRO C MANNOSYLALANINE; AMINO ACID DERIVATIVE; CARBOHYDRATE; ESTER DERIVATIVE; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CLAISEN REARRANGEMENT; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037064620     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01225-5     Document Type: Article

References (40)

1. (a) Postema M.H.D. Tetrahedron. 48:1992;8545.
2. (b) Levy D.E., Tang C. The Chemistry of C-Glycosides. 1995;Pergamon, Oxford.
3. © Postema M.H.D. C-Glycoside Synthesis. 1995;CRC, USA.
4. (d) Togo H., He W., Waki Y., Yokoyama M. Synlett. 1998;700.
5. (a) Ravishankar R., Surolia A., Vijayan M., Lim S., Kishi Y. J. Am. Chem. Soc. 120:1998;11297.
6. (b) Wang J., Kovac P., Sinaÿ P., Gluademans C.P. J. Carbohydr. Res. 308:1998;191.
7. For recent reviews see: (a) Dondoni A., Marra A. Chem. Rev. 100:2000;4395.
8. (b) Schweizer F. Angew. Chem. Int. Ed. 41:2002;230.
9. Maracurelle L.A., Bertozzi C.R. Chem. Eur. J. 5:1999;1384.
10. (a) Bar T., Schmidt R.R. Liebigs Ann. Chem. 1991;185.
11. (b) Sparks M.A., Williams K.W., Whitesides G.M. J. Med. Chem. 36:1993;78.
12. (a) Bertozzi C.R., Hoeprich P.D. Jr., Bednarsky M.D. J. Org. Chem. 57:1992;6092.
13. (b) O'Neil K.T., DeGrado W.F. Science. 250:1990;646.
14. (a) Veber D.F., Freidinger R.M. Trends Neurosci. 8:1985;392.
15. (b) Goodman M., Zhang J. Chemtracts. 10:1997;629.
16. © Mossel E., Formaggio F., Crisma M., Toniolo C., Broxterman Q.B., Boesten W.H., Kamphuis J., Quaedflieg P.J.L.M., Temussi P. Tetrahedron: Asymmetry. 8:1997;1305.
17. (d) Bellier B., McCort-Tranchepain I., Ducos B., Danascimento S., Meudal H., Noble F., Garbay C., Roques B.P. J. Med. Chem. 40:1997;3947
18. (e) Cativiela C., Daz-de-Villegas M.D. Tetrahedron: Asymmetry. 9:1998;3517. and references therein.
19. Schweizer F., Inazu T. Org. Lett. 3:2001;4115.
20. Dondoni A., Junquera F., Merchan F.L., Merino P., Scherrmann M.-C., Tejero T. J. Org. Chem. 62:1997;5484.
21. Simchen G., Pürner E. Synthesis. 1990;525.
22. Rosenthal A., Brink A.J. J. Carbohydr. Nucleosides, Nucleotides. 2:1975;343.
23. Colombo L., Casiraghi G., Rassu G., Pittalis A. J. Org. Chem. 56:1991;3897.
24. (a) Engel N., Kübel B., Steglich W. Angew. Chem. Int. Ed. 16:1977;394
25. (b) Kübel B., Hofle G., Steglich W. Angew. Chem. Int. Ed. 14:1975;58.
26. [3,3]-Sigmatropic rearrangements: (a) Tlshian D.B., Freaser-Reid B. J. Org. Chem. 49:1984;518.
27. (b) Ireland R.E., Wuts P.G.M., Ernst B.J. J. Am. Chem. Soc. 103:1981;3205.
28. © Ireland R.E., Smith M.G. J. Am. Chem. Soc. 110:1998;854.
29. (d) Curran D.P., Suh Y.J. Carbohydr. Res. 171:1987;161.
30. (e) Vidal T., Haudrechy A., Langlois Y. Tetrahedron Lett. 40:1999;5677.
31. (f) Godage H.Y., Fairbanks A.J. Tetrahedron Lett. 41:2000;7589. [1,2]- and [1,4]-Wittig rearrangement
32. (g) Tomooka K., Yamamoto H., Nakai T. Angew. Chem. Int. Ed. 39:2000;4500.
33. (a) Jakel C., Dotz K.H. J. Organomet. Chem. 624:2001;172
34. (b) Kan C., Long C.M., Paul M., Ring C.M., Tully S.E., Rojas C.M. Org. Lett. 3:2001;381.
35. N2' attack on the C1 position. Such reactivity has been documented: Ramesh N.G., Balasubramanian K.K. Tetrahedron. 51:1992;255. and references therein.
36. It is known that the formation of the rearranged urea is favored at high pH: (a) Moore J.S., Stupp S.I. Macromolecules. 23:1990;2365. See also
37. (b) Hawker C.J., Fréchet J.M.J. J. Am. Chem. Soc. 114:1992;8405.
38. (a) Sears P., Wong C.-H. Angew. Chem. Int. Ed. 38:1999;2300.
39. (b) Simanek E.E., McGarvey G.J., Jablonowsky J.A., Wong C.-H. Chem. Rev. 98:1998;833
40. © Roche D., Bänteli R., Winkler T., Casset F., Ernst B. Tetrahedron Lett. 39:1998;2545.