An easy route to seven-membered iminocyclitols from aldohexopyranosyl enamines

Tetrahedron Asymmetry

Volumn 13, Issue 16, 2002, Pages 1743-1753

  Fuentes, José ^a   Gasch, Consolación ^a   Olano, David ^b   Pradera, M Angeles ^a   Repetto, Guillermo ^b   Sayago, Francisco J ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

^b Biology Section Apdo 863 E 41080   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,6 ANHYDRO 2,3,4 TRI O ACETYL N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO GLUCOPYRANOSYLAMINE; 1,6 ANHYDRO 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO GALACTOPYRANOSYLAMINE; 1,6 ANHYDRO 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO GLUCOPYRANOSYLAMINE; 1,6 ANHYDRO 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO MANNOPYRANOSYLAMINE; 1,6 ANHYDRO N (2,2 DIETHOXYCARBONYLVINYL) 2,3,4 TRI O MESYL BETA DEXTRO GALACTOPYRANOSYLAMINE; 1,6 ANHYDRO N (2,2 DIETHOXYCARBONYLVINYL) 2,3,4 TRI O MESYL BETA DEXTRO GLUCOPYRANOSYLAMINE; 1,6 ANHYDRO N (2,2 DIETHOXYCARBONYLVINYL) 2,3,4 TRI O MESYL BETA DEXTRO MANNOPYRANOSYLAMINE; 1,6 ANHYDRO N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO GALACTOPYRANOSYLAMINE; 1,6 ANHYDRO N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO GLUCOPYRANOSYLAMINE; 1,6 ANHYDRO N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO MANNOPYRANOSYLAMINE; 2,3,4 TRI O ACETYL N (2,2 DIETHOXYCARBONYLVINYL) 6 O MESYL BETA DEXTRO GLUCOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) 6 O MESYL BETA DEXTRO GALACTOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) 6 O MESYL BETA DEXTRO GLUCOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) 6 O MESYL BETA DEXTRO MANNOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) 6 O TRITYL BETA DEXTRO GALACTOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) 6 O TRITYL BETA DEXTRO MANNOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO GALACTOPYRANOSYLAMINE; 2,3,4 TRI O BENZOYL N (2,2 DIETHOXYCARBONYLVINYL) BETA DEXTRO MANNOPYRANOSYLAMINE; CYANOBOROHYDRIDE SODIUM; ENAMINE; GLYCOSIDASE; N (2,2 DIETHOXYCARBONYLVINYL) 2,3,4,6 TETRA O MESYL BETA DEXTRO GALACTOPYRANOSYLAMINE; N (2,2 DIETHOXYCARBONYLVINYL) 2,3,4,6 TETRA O MESYL BETA DEXTRO GLUCOPYRANOSYLAMINE; N (2,2 DIETHOXYCARBONYLVINYL) 2,3,4,6 TETRA O MESYL BETA DEXTRO MANNOPYRANOSYLAMINE; PYRAN DERIVATIVE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DEPROTECTION REACTION; DRUG ACTIVITY; DRUG CONFORMATION; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY;

EID: 0037183385     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00377-4     Document Type: Article

References (37)

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2. For reviews see: (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384; (b) Wong, C. H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521-546; (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515-553; (c) Asano, N.; Oseki, H.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701-3706.
3. For reviews see: (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384; (b) Wong, C. H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521-546; (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515-553; (c) Asano, N.; Oseki, H.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701-3706.
4. For reviews see: (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384; (b) Wong, C. H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521-546; (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515-553; (c) Asano, N.; Oseki, H.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701-3706.
5. See as examples: (a) Kiess, F. M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119-120; (b) Blanco, M. J.; Sardina, F. J. J. Org. Chem. 1998, 63, 3411-3416; (c) Wehner, V.; Jäger, V. Angew. Chem., Int. Ed. Engl. 1990, 29, 1169-1171; (d) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Biorg. Med. Chem. Lett. 1997, 7, 893-896; (e) Fuentes, J.; Olano, D.; Pradera, M. A. Tetrahedron: Asymmetry 1997, 8, 3443-3456; (f) Hummer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis 1997, 634-642; Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033-1044.
6. See as examples: (a) Kiess, F. M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119-120; (b) Blanco, M. J.; Sardina, F. J. J. Org. Chem. 1998, 63, 3411-3416; (c) Wehner, V.; Jäger, V. Angew. Chem., Int. Ed. Engl. 1990, 29, 1169-1171; (d) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Biorg. Med. Chem. Lett. 1997, 7, 893-896; (e) Fuentes, J.; Olano, D.; Pradera, M. A. Tetrahedron: Asymmetry 1997, 8, 3443-3456; (f) Hummer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis 1997, 634-642; Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033-1044.
7. See as examples: (a) Kiess, F. M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119-120; (b) Blanco, M. J.; Sardina, F. J. J. Org. Chem. 1998, 63, 3411-3416; (c) Wehner, V.; Jäger, V. Angew. Chem., Int. Ed. Engl. 1990, 29, 1169-1171; (d) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Biorg. Med. Chem. Lett. 1997, 7, 893-896; (e) Fuentes, J.; Olano, D.; Pradera, M. A. Tetrahedron: Asymmetry 1997, 8, 3443-3456; (f) Hummer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis 1997, 634-642; Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033-1044.
8. See as examples: (a) Kiess, F. M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119-120; (b) Blanco, M. J.; Sardina, F. J. J. Org. Chem. 1998, 63, 3411-3416; (c) Wehner, V.; Jäger, V. Angew. Chem., Int. Ed. Engl. 1990, 29, 1169-1171; (d) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Biorg. Med. Chem. Lett. 1997, 7, 893-896; (e) Fuentes, J.; Olano, D.; Pradera, M. A. Tetrahedron: Asymmetry 1997, 8, 3443-3456; (f) Hummer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis 1997, 634-642; Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033-1044.
9. See as examples: (a) Kiess, F. M.; Poggendorf, P.; Picasso, S.; Jäger, V. Chem. Commun. 1998, 119-120; (b) Blanco, M. J.; Sardina, F. J. J. Org. Chem. 1998, 63, 3411-3416; (c) Wehner, V.; Jäger, V. Angew. Chem., Int. Ed. Engl. 1990, 29, 1169-1171; (d) Kraehenbuehl, K.; Picasso, S.; Vogel, P. Biorg. Med. Chem. Lett. 1997, 7, 893-896; (e) Fuentes, J.; Olano, D.; Pradera, M. A. Tetrahedron: Asymmetry 1997, 8, 3443-3456; (f) Hummer, W.; Dubois, E.; Gracza, T.; Jäger, V. Synthesis 1997, 634-642; Farr, R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033-1044.
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