Synthesis of the amino sugar from C-1027

Organic Letters

Volumn 3, Issue 15, 2001, Pages 2403-2406

  Semmelhack, M F ^a   Jiang, Yu ^a   Ho, Douglas ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; AMINOSUGAR; ANTIBIOTIC C 1027; ANTIINFECTIVE AGENT; ENEDIYNE; MANNOSE;

ARTICLE; CHEMISTRY; SYNTHESIS;

AMINO SUGARS; AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; ENEDIYNES; MANNOSE;

EID: 0035954885     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010119s     Document Type: Article

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31. 5).
32. A few other examples of a β-lactam fused to a pyranose have been examined by X-ray crystallography, but none with the orientation of substitutents (4-amino-5-acyl) of 23. Preparation by a Mitsunobu reaction produced a 4-amino-3-acyl lactam: Zegrodka, O.; Abramski, W.; Urbanczyk-Lipowska, Z.; Chmielewski, M. Carbohydr. Res. 1998, 307, 33. Preparation by a cycloaddition to a glycal produced a 2-amino-3-acyl lactam: Chmielewski, M.; Kaluza, Z.; Suwinska, K.; Rosenbaum, D.; Duddek, H.; Magnus, P. D.; Huffman, J. C. Carbohydr. Res. 1990, 203, 183. Assembly of the pyranose ring onto a β-lactam gave a 3-amino-4-acyl derivative: Hart, D. J.; Leroy, V.; Merriman, G. H.; Young, D. G. J. J. Org. Chem. 1992, 57, 5670.
33. A few other examples of a β-lactam fused to a pyranose have been examined by X-ray crystallography, but none with the orientation of substitutents (4-amino-5-acyl) of 23. Preparation by a Mitsunobu reaction produced a 4-amino-3-acyl lactam: Zegrodka, O.; Abramski, W.; Urbanczyk-Lipowska, Z.; Chmielewski, M. Carbohydr. Res. 1998, 307, 33. Preparation by a cycloaddition to a glycal produced a 2-amino-3-acyl lactam: Chmielewski, M.; Kaluza, Z.; Suwinska, K.; Rosenbaum, D.; Duddek, H.; Magnus, P. D.; Huffman, J. C. Carbohydr. Res. 1990, 203, 183. Assembly of the pyranose ring onto a β-lactam gave a 3-amino-4-acyl derivative: Hart, D. J.; Leroy, V.; Merriman, G. H.; Young, D. G. J. J. Org. Chem. 1992, 57, 5670.
34. A few other examples of a β-lactam fused to a pyranose have been examined by X-ray crystallography, but none with the orientation of substitutents (4-amino-5-acyl) of 23. Preparation by a Mitsunobu reaction produced a 4-amino-3-acyl lactam: Zegrodka, O.; Abramski, W.; Urbanczyk-Lipowska, Z.; Chmielewski, M. Carbohydr. Res. 1998, 307, 33. Preparation by a cycloaddition to a glycal produced a 2-amino-3-acyl lactam: Chmielewski, M.; Kaluza, Z.; Suwinska, K.; Rosenbaum, D.; Duddek, H.; Magnus, P. D.; Huffman, J. C. Carbohydr. Res. 1990, 203, 183. Assembly of the pyranose ring onto a β-lactam gave a 3-amino-4-acyl derivative: Hart, D. J.; Leroy, V.; Merriman, G. H.; Young, D. G. J. J. Org. Chem. 1992, 57, 5670.