Divergent synthesis of 3-amino-3-deoxy- and 4-amino-4-deoxyhexoses

Tetrahedron

Volumn 52, Issue 13, 1996, Pages 4829-4838

  Spanu, Pietro ^a   Rassu, Gloria ^a   Ulgheri, Fausta ^a   Zanardi, Franca ^b   Battistini, Lucia ^b   Casiraghi, Giovanni ^b  

^a Ist l'Applic Tecniche Chimiche A   (Italy)

^b V le delle Scienze   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029964528     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00151-2     Document Type: Article

References (14)

1. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677.
2. Golebiowski, A.; Jurczak, J. Synlett 1993, 241. Kiciak, K.; Jacobsson, U.; Golebiowski, A.; Jurczak, J. Polish J. Chem. 1994, 68, 199. Jurczak, J.; Golebiowski, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier B. V.; Amsterdam, 1989; Vol. 4, p 111. Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
3. Golebiowski, A.; Jurczak, J. Synlett 1993, 241. Kiciak, K.; Jacobsson, U.; Golebiowski, A.; Jurczak, J. Polish J. Chem. 1994, 68, 199. Jurczak, J.; Golebiowski, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier B. V.; Amsterdam, 1989; Vol. 4, p 111. Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
4. Golebiowski, A.; Jurczak, J. Synlett 1993, 241. Kiciak, K.; Jacobsson, U.; Golebiowski, A.; Jurczak, J. Polish J. Chem. 1994, 68, 199. Jurczak, J.; Golebiowski, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier B. V.; Amsterdam, 1989; Vol. 4, p 111. Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
5. Golebiowski, A.; Jurczak, J. Synlett 1993, 241. Kiciak, K.; Jacobsson, U.; Golebiowski, A.; Jurczak, J. Polish J. Chem. 1994, 68, 199. Jurczak, J.; Golebiowski, A. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier B. V.; Amsterdam, 1989; Vol. 4, p 111. Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
6. Casiraghi, G.; Rassu, G. Synthesis 1995, 607, and references therein.
7. Horton, D.; Wander, J. D. In The Carbohydrates, Chemistry and Biochemistry, Pigman W.; Horton, D.; Wander, J. D., Eds.; Academic Press: New York, 1980; Vol. 1 B, p 643. Pelyvas, I. F.; Monneret, C.; Herczegh, P. Synthetic Aspects of Aminodeoxy Sugars of Antibiotics; Springer: Berlin, 1988.
8. Horton, D.; Wander, J. D. In The Carbohydrates, Chemistry and Biochemistry, Pigman W.; Horton, D.; Wander, J. D., Eds.; Academic Press: New York, 1980; Vol. 1 B, p 643. Pelyvas, I. F.; Monneret, C.; Herczegh, P. Synthetic Aspects of Aminodeoxy Sugars of Antibiotics; Springer: Berlin, 1988.
9. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760. Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Gasparri Fava, G.; Belicchi Ferrari, M.; Pelosi G. Tetrahedron Asymmetry 1992, 5, 1035.
10. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760. Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Gasparri Fava, G.; Belicchi Ferrari, M.; Pelosi G. Tetrahedron Asymmetry 1992, 5, 1035.
11. The absence of any contact between H(1) and H(2) in the NOESY spectrum of 20 firmly establishes the trans location for these protons.
12. Schmid, C. R.; Bryant, J. D. Org. Synth. 1995, 72, 6.
13. The N-acetyl derivative of 13, namely 3-acetamido-3-deoxy-D-altrose, was previously synthesized: Coxon, B.; Hough, L. J. Chem. Soc. 1961, 1463.
14. Koto, S.; Kawakatsu, N.; Zen, S. Bull. Chem. Soc. Japan 1973, 46, 876.