SCOPUS 정보 검색 플랫폼

Tetrahedron Asymmetry

Volumn 8, Issue 12, 1997, Pages 1971-1974

Fragmentation of carbohydrate anomeric alkoxy radicals. Synthesis of azasugars

(4) Francisco, Cosme G a Freire, Raimundo a González, Concepción C a Suárez, Ernesto a

a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030919816 PISSN: 09574166 EISSN: None Source Type: Journal
DOI: 10.1016/S0957-4166(97)00188-2 Document Type: Article

Times cited : (34)

References (27)

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4
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- Poitout, L.¹ Lemerrer, Y.² Depezay, J.C.³

5
- 0027954984
- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1994) Tetrahedron Lett. , vol.35 , pp. 359-362
- Henderson, I.¹ Laslo, K.² Wong, C.-H.³

6
- 0027496038
- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1993) J. Org. Chem. , vol.55 , pp. 4809-4812
- Takaoka, Y.¹ Kajimoto, T.² Wong, C.-H.³

7
- 0027499972
- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1993) Tetrahedron , vol.49 , pp. 2939-2958
- Dondoni, A.¹ Merino, P.² Perrone, D.³

8
- 0027176072
- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1993) Tetrahedron Lett. , vol.34 , pp. 3613-3616
- Furneaux, R.H.¹ Tyler, P.C.² Whitehouse, L.A.³

9
- 0026554003
- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1992) Tetrahedron , vol.48 , pp. 3365-3376
- Fairbanks, A.J.¹ Carpenter, N.C.² Fleet, G.W.J.³ Ramsden, N.G.⁴ Cenci De Bello, I.⁵ Winchester, B.G.⁶ Al-Daher, S.S.⁷ Nagahashi, G.⁸

10
- 0025002377
- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1990) J. Org. Chem. , vol.55 , pp. 3926-3932
- Straub, A.¹ Effenberger, F.² Fischer, P.³

11
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- For recent references see, inter alia: Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697-706; Ganem, B. Acc. Chem. Res. 1996, 29, 340-347; Cipolla, L.; Lay, L.; Nicostra, F.; Pangrazio, C.; Panza, L. Tetrahedron 1995, 51, 4679-4690; Poitout, L.; Lemerrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1609-1612; Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359-362; Takaoka, Y.; Kajimoto, T.; Wong, C.-H. J. Org. Chem. 1993, 55, 4809-4812; Dondoni, A.; Merino, P.; Perrone, D. Tetrahedron 1993, 49, 2939-2958; Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613-3616; Fairbanks, A. J.; Carpenter, N. C.; Fleet, G. W. J.; Ramsden, N. G.; Cenci de Bello, I.; Winchester, B. G.; Al-Daher, S. S.; Nagahashi, G. Tetrahedron. 1992, 48, 3365-3376; Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926-3932; Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron Lett. 1988, 29, 2871-2874.
- (1988) Tetrahedron Lett. , vol.29 , pp. 2871-2874
- Fleet, G.W.J.¹ Ramsden, N.G.² Witty, D.R.³

12
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- Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210; Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182-190; Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135-162.
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15
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- (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 772-1114
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16
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- (b) Armas, P.; Francisco, C. G.; Suarez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866; Armas, P.; Francisco, C. G.; Suarez, E. Tetrahedron Lett. 1993, 34, 7331-7334; Francisco, C. G.; Gonzalez, C. C.; Suarez, E. Tetrahedron Lett. 1996, 37, 1687-1690.
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17
- 0027363422
- (b) Armas, P.; Francisco, C. G.; Suarez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866; Armas, P.; Francisco, C. G.; Suarez, E. Tetrahedron Lett. 1993, 34, 7331-7334; Francisco, C. G.; Gonzalez, C. C.; Suarez, E. Tetrahedron Lett. 1996, 37, 1687-1690.
- (1993) Tetrahedron Lett. , vol.34 , pp. 7331-7334
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18
- 0343182983
- (b) Armas, P.; Francisco, C. G.; Suarez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866; Armas, P.; Francisco, C. G.; Suarez, E. Tetrahedron Lett. 1993, 34, 7331-7334; Francisco, C. G.; Gonzalez, C. C.; Suarez, E. Tetrahedron Lett. 1996, 37, 1687-1690.
- (1996) Tetrahedron Lett. , vol.37 , pp. 1687-1690
- Francisco, C.G.¹ Gonzalez, C.C.² Suarez, E.³

19
- 0028945715
- Duvoid, T.; Francis, G. W.; Papaioannou, D. Tetrahedron Lett. 1995, 36, 3153-3156.
- (1995) Tetrahedron Lett. , vol.36 , pp. 3153-3156
- Duvoid, T.¹ Francis, G.W.² Papaioannou, D.³

20
- 84989531500
- Viaud, M. C.; Rollin, P. Synthesis 1990, 130-132.
- (1990) Synthesis , pp. 130-132
- Viaud, M.C.¹ Rollin, P.²

21
- 0342649078
- note
- 6N: C, 54.35; H, 7.37; N, 4.88. Found: C, 54.25; H, 7.37; N, 4.89.

22
- 0343083239
- note
- 7NP: C, 57.28; H, 5.29; N, 3.34. Found: C, 57.44; H, 5.46; N, 3.25.

23
- 0029030535
- Ichikawa, Y.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 4585-4586.
- (1995) Tetrahedron Lett. , vol.36 , pp. 4585-4586
- Ichikawa, Y.¹ Igarashi, Y.²

24
- 0343955182
- note
- 6N: C, 59.81; H, 5.96; N, 4.36. Found: C, 59.74; H, 6.05; N, 4.30.

25
- 0343519365
- note
- 7N: C, 52.65; H, 7.89; N, 4.39. Found: C, 52.56; H, 7.84; N. 4.01.

26
- 0343519364
- note
- MMX force field as implemented in PCMODEL (v. 4.0), Serena Software, Bloomington IN, 47402-3076.

27
- 0000644818
- Saltzman, H.; Sharefkin, J. G. Org. Synth., Coll. Vol. V, 1973, pp. 658-659.
- (1973) Org. Synth., Coll. , vol.5 , pp. 658-659
- Saltzman, H.¹ Sharefkin, J.G.²

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