Synthesis of N-unsubstituted, mono- and disubstituted carbohydrate-1-O- carbamates and their behaviour in glycoside syntheses

Carbohydrate Research

Volumn 339, Issue 18, 2004, Pages 2821-2833

  Knoben, Hans Peter ^a   Schlüter, Urs ^a   Redlich, Hartmut ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Carbohydrate 1 carbamates; Disaccharides; Glycosidation; Glycosyl carbamates; One pot reaction

Indexed keywords

ANOMERIC RATIOS; CARBAMATE FUNCTIONS; GLYCOSIDES;

AROMATIC COMPOUNDS; DATA REDUCTION; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

CARBOHYDRATES;

CARBAMIC ACID DERIVATIVE; CARBOHYDRATE; GLYCOSIDE;

ARTICLE; PRIORITY JOURNAL; SYNTHESIS;

CARBAMATES; GLUCOSIDES; GLYCOSIDES; METHODS;

EID: 9944230907     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.10.002     Document Type: Article

References (32)

1. T.W. Greene, and P.G.M. Wuts Protecting Groups in Organic Synthesis 1991 Wiley New York
2. H. Kunz, and J. Zimmer Tetrahedron Lett. 34 1993 2907 2910
3. R.J. Hinklin, and L.L. Kiessling J. Am. Chem. Soc. 123 4 2001 3379 3380
4. D. Plusquellec, F. Roulleau, and E. Brown Tetrahedron Lett. 25 1984 1901 1904
5. D. Plusquellec, and M. Lefeuvre Tetrahedron Lett. 28 1987 4165 4168
6. R.G.G. Lenders, R. Ruytenbeek, E.W.P. Damen, and H.W. Scheeren Synthesis 1996 1309 1312
7. C. Prata, N. Mora, J.-M. Lacombe, J.C. Maurizis, and B. Pucci Tetrahedron Lett. 38 51 1997 8859 8862
8. C. Prata, N. Mora, J.-M. Lacombe, J.C. Maurizis, and B. Pucci Carbohydr. Res. 321 1999 4 14
9. T.D. Perrine, C.P.J. Claudemans, R.K. Ness, J. Kyle, and H.G. Fletcher Jr. J. Org. Chem. 32 1967 664 669
10. R. Eby, S.J. Sondheimer, and C. Schuerch Carbohydr. Res. 73 1979 273 276
11. J.-I. Sakai, T. Takeda, and Y. Ogihara Carbohydr. Res. 95 1981 125 131
12. S.K. Chaudhary, and O. Hernandez Tetrahedron Lett. 1 1979 95 98
13. M. Bessodes, D. Komiotis, and K. Antonakis Tetrahedron Lett. 27 1986 579 580
14. 15th ed. Organikum 1984 Deutscher Verlag der Wissenschaften Berlin pp 511-512
15. O.T. Schmidt Methods Carbohydr. Chem. 2 1963 318 325
16. R.R. Schmidt, and J. Michel Angew. Chem. 92 1980 763 764
17. R.R. Schmidt, and J. Michel Angew. Chem., Int. Ed. Engl. 19 1980 731
18. When an excess of ethyl isocyanates is used with carbohydrate derivatives 4, 5 and 6 or allyl isocyanate with 6 the formation of the corresponding allophanates is obtained within 60 min in 90% yield under typical reaction conditions (method D)
19. H.A. Staab Liebigs Ann. Chem. 609 1957 83 88
20. H.A. Staab Angew. Chem. 12 1962 407 423
21. H.A. Staab Angew. Chem., Int. Ed. Engl. 1 1962 351 367
22. R.R. Schmidt Adv. Carbohydr. Chem. 50 1994 21
23. M.J. Ford, and S.V. Ley Synlett 1990 255 256
24. R.G. Pearson J. Am. Chem. Soc. 85 1963 3533 3539
25. R.G. Pearson Coord. Chem. Rev. 100 1990 403 425
26. S. Hanessian, C. Baquet, and N. Lehong Carbohydr. Res. 80 1980 C17 C22
27. B. Fraser-Reid, P. Konradsson, D.R. Mootoo, and U.E. Udodong J. Chem. Soc., Chem. Commun. 1988 823 825
28. J.-M. Mallet, G. Meyer, F. Yvelin, A. Jutand, C. Amatore, and P. Sinaÿ Carbohydr. Res. 244 1993 237 246
29. J.M. Küster, and I. Dyong Liebigs Ann. Chem. 1975 2179 2189
30. H.S. Isbell Annu. Rev. Biochem. 9 1940 65 92
31. See, for example: R.U. Lemieux Adv. Carbohydr. Chem. 9 1954 1 57
32. 2