A stereoselective synthesis of N-β-D-glycosyl amides by a Ritter-type reaction

Synlett

Volumn , Issue 20, 2006, Pages 3451-3454

  Song, Xuezheng ^a   Hollingsworth, Rawle I ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

Amidation; Glycosyl amide; Ritter reaction

Indexed keywords

ACETAMIDE DERIVATIVE; ACETONITRILE; AMIDE; LEWIS ACID; MONOSACCHARIDE; N (2,3,4,6 TETRA O ACETYL BETA DEXTRO GALACTOSYL)ACETAMIDE; N (2,3,4,6 TETRA O ACETYL BETA DEXTRO GLUCOSYL)ACETAMIDE; N (2,3,4,6 TETRA O ACETYL BETA DEXTRO MANNOSYL)ACETAMIDE; N (2,3,4,6 TETRA O TRIMETHYLACETYL BETA DEXTRO GLUCOSYL)ACETAMIDE; N BETA DEXTRO GLYCOSYL AMIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33846553079     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958417     Document Type: Article

References (21)

1. Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045.
2. Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593.
3. (a) Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1989, 1805.
4. (b) Ratcliffe, A. J.; Konradsson, P.; Fraser-Reid, B. Carbohydr. Res. 1991, 216, 323.
5. (c) Handlon, A. L.; Fraser-Reid, B. J. Am. Chem. Soc. 1993, 115, 3796.
6. (d) Ratcliffe, A. J.; Mootoo, D. R.; Andrews, C. W.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 7661.
7. (e) Nair, L. G.; Fraser-Reid, B.; Szardenings, A. K. Org. Lett. 2001, 3, 317.
8. (a) Likhoshertov, L. M.; Novikova, V. A.; Dervitskaja, V. A.; Kochetkov, N. K. Carbohydr. Res. 1986, 46, C1.
9. (b) Lubineau, A.; Auge, J.; Drouillat, B. Carbohydr. Res. 1995, 266, 211.
10. (c) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
11. (d) Dorsey, A. D.; Barbarow, J. E.; Trauner, D. Org. Lett. 2003, 5, 3237.
12. (e) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408.
13. (f) Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234.
14. (g) Tanaka, H.; Iwata, Y.; Takahashi, D.; Adachi, M.; Takahashi, T. J. Am. Chem. Soc. 2005, 127, 1630.
15. (a) Pleuss, N.; Kunz, H. Angew. Chem. Int. Ed. 2003, 42, 3174.
16. (b) Pleuss, N.; Kunz, H. Synthesis 2005, 122.
17. (a) Pavia, A. A.; Ung-Chhun, S. A.; Durand, J.-L. J. Org. Chem. 1981, 46, 3158.
18. (b) Noort, D.; van der Marel, G. A.; Mulder, G. J.; van Boom, J. H. Synlett 1992, 224.
19. (c) Jiménez Blanco, J. L.; Rubio, E. M.; Ortiz Mellet, C.; Garcia Fernández, J. M. Synlett 2004, 2230.
20. (a) Schweizer, F.; Lohse, A.; Otter, A.; Hindsgaul, O. Synlett 2001, 1434.
21. (b) Lohse, A.; Schweizer, F.; Hindsgaul, O. Comb. Chem. High Throughput Screening 2002, 5, 389.