Synthesis of alditols by reductive radical fragmentation of N-phthalimido glycosides. Preparation of chiral synthetic intermediates

Tetrahedron Letters

Volumn 40, Issue 42, 1999, Pages 7525-7528

  Martín, Angeles ^a   Rodríguez, María S ^b   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDITOL; CARBOHYDRATE DERIVATIVE; FURAN DERIVATIVE; GLYCOSIDE; NITRIC ACID DERIVATIVE; PYRANOSIDE; RADICAL;

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; PRECURSOR; SYNTHESIS;

EID: 0033570273     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01482-3     Document Type: Article

References (18)

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2. Francisco, C. G.; Léon, E. I.; Moreno, P.; Suárez, E. Tetrahedron: Asymmetry 1998, 9, 2975-2978. For the same reaction under oxidative conditions see: Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774. Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866. Francisco, C. G.; Martín, C. G.; Suárez, E. J. Org. Chem. 1998, 63, 8092-8093.
3. Francisco, C. G.; Léon, E. I.; Moreno, P.; Suárez, E. Tetrahedron: Asymmetry 1998, 9, 2975-2978. For the same reaction under oxidative conditions see: Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774. Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866. Francisco, C. G.; Martín, C. G.; Suárez, E. J. Org. Chem. 1998, 63, 8092-8093.
4. Francisco, C. G.; Léon, E. I.; Moreno, P.; Suárez, E. Tetrahedron: Asymmetry 1998, 9, 2975-2978. For the same reaction under oxidative conditions see: Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774. Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866. Francisco, C. G.; Martín, C. G.; Suárez, E. J. Org. Chem. 1998, 63, 8092-8093.
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9. (a) Mitsunobu, O. Synthesis 1981, 1-28. (b) Grochowski, E.; Jurczak, J. Synthesis 1976, 682-684. (c) Jurczak, J.; Grochowski, E. In International Symposium on Phosphorus Chemistry Directed Towards Biology, Burzenin, Poland, 1979; Stec, W. J., Ed.; Franklin Book Company, 1980; p. 54.
10. (a) Mitsunobu, O. Synthesis 1981, 1-28. (b) Grochowski, E.; Jurczak, J. Synthesis 1976, 682-684. (c) Jurczak, J.; Grochowski, E. In International Symposium on Phosphorus Chemistry Directed Towards Biology, Burzenin, Poland, 1979; Stec, W. J., Ed.; Franklin Book Company, 1980; p. 54.
11. 4 and concentrated under reduced pressure. Chromatotron chromatography was used to purify the residue.
12. 3CN, washed with n-hexane and concentrated under reduced pressure. Chromatotron chromatography was used to purify he residue.
13. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Le Merre, Y.; Gravier-Pelletier, C.; Dumas, J.; Depezay, J. C. Tetrahedron Lett. 1990, 31, 1003-1006. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
14. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Le Merre, Y.; Gravier-Pelletier, C.; Dumas, J.; Depezay, J. C. Tetrahedron Lett. 1990, 31, 1003-1006. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
15. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Le Merre, Y.; Gravier-Pelletier, C.; Dumas, J.; Depezay, J. C. Tetrahedron Lett. 1990, 31, 1003-1006. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
16. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
17. Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H. K.; Mikkilineni, A. B.; Wu, D. C.-J.; Saibaba, R.; Panzica, R. P. J. Org. Chem. 1988, 53, 2598-2602. Pottie, M.; Van der Eycken, J.; Röper, H.; Vandewalle, M. Tetrahedron: Asymmetry 1991, 2, 329-330. Pottie, M.; De Lathauwer, G.; Vandewalle, M. Bull. Soc. Chim. Belg. 1994, 103, 285-294. Flasche, M.; Scharf, H.-D. Tetrahedron: Asymmetry 1995, 6, 1543-1546.
18. A similar transesterification has been observed during the hydrolysis of 1,2,3-tri-O-acetyl-5-O-(tert-butyldimethyl)silyl-4-O-formyl-D-arabinitol synthesised in Ref. 1.