Synthesis of 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid, a key precursor of a stereoregular polyamide

Journal of Carbohydrate Chemistry

Volumn 20, Issue 7-8, 2001, Pages 689-701

  Zaliz, Carmen L Romero ^a   Varela, Oscar ^a  

^a DEPARTAMENTO DE QUÍMICA ORGÁNICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035648008     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108283     Document Type: Article

References (25)

1. th birthday.
2. Varela, O.; Orgueira, H. A. Synthesis of Chiral Polyamides from Carbohydrate Derived Monomers. Adv. Carbohydr. Chem. Biochem. 1999, 55, 137-174.
3. Gonsalves, K. E.; Mungara, P. M. Synthesis and Properties of Degradable Polyamides and Related Polymers. Trends Polym. Sci. 1996, 4, 25-31.
4. Thiem, J.; Bachmann, F. Carbohydrate-derived Polyamides. Trends Polym. Sci. 1994, 2, 425-432.
5. Orgueira, H. A.; Varela, O. Stereocontrolled Synthesis of Stereoregular, Chiral Analogs of Nylon 5,5 and Nylon 5,6. Tetrahedron: Asymmetry 1997, 8, 1383-1389.
6. Orgueira, H. A.; Erra-Balsells, R.; Nonami, H.; Varela, O. Synthesis of Chiral Polyhydroxy Polyamides Having Chains of Defined Regio and Stereoregularity. Macromolecules 2001, 34, 687-695.
7. Orgueira, H. A.; Varela, O. Synthesis and Characterization of Stereoregular AABB-Type Polymannaramides. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1024-1030.
8. Zamora, F.; Bueno, M.; Molina, I.; Orgueira, H. A.; Varela, O.; Galbis, J. A. Synthesis of Carbohydrate-based Monomers that are Precursors for the Preparation of Stereoregular Polyamides. Tetrahedron: Asymmetry 1996, 7, 1811-1818.
9. Bueno, M.; Zamora, F.; Molina, I.; Orgueira, H. A.; Varela, O.; Galbis, J. A. Synthesis and Characterization of Optically Active Polyamides Derived from Carbohydratebased Monomers. J. Polym. Sci., Part A: Polym. Chem. 1997, 55, 3645-3653.
10. Bueno Martínez, M.; Zamora Mata, F.; Ugalde Donoso, M. T.; Galbis Pérez, J. A. Some Derivatives of 6-Amino-6-deoxy-D-gluconic acid that are Precursors for the Synthesis of Polyamides. Carbohydr. Res. 1992, 230, 191-195.
11. Bueno, M.; Galbis, J. A.; García-Martín. M. G.; de Paz, M. V.; Zamora, F.; Muñoz-Guerra, S. Synthesis of Stereoregular Polygluconamides from D-Glucose and D-Glucosamine. J. Polym. Sci., Part A: Polym. Chem. 1995, 33, 299-305.
12. Kefur, K.; Kefurtova, Z.; Jary, J. 6-amino-6-deoxyhexonolactams. Collect. Czech. Chem. Commun. 1988, 53, 1795-1805, and references therein.
13. Kiely, D. E.; Chang, L.; Lin, T. H. Synthetic Polyhydroxypolyamides from Galactaric, Xylaric, D-Glucaric, and D-Mannaric Acids and Alkylenediamine Monomers -Some Comparisons. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 594-603.
14. Schmidt, O. T. Isopropylidene Derivatives. In Methods in Carbohydrate Chemistry, Vol II, Academic, New York, 1963, 324. Calinaud, P.; Gelas, J. Synthesis of Isopropylidene, Benzylidene, and Related Acetals. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker, New York, 1996, 21.
15. Schmidt, O. T. Isopropylidene Derivatives. In Methods in Carbohydrate Chemistry, Vol II, Academic, New York, 1963, 324. Calinaud, P.; Gelas, J. Synthesis of Isopropylidene, Benzylidene, and Related Acetals. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker, New York, 1996, 21.
16. Chen, S. Y.; Joullié, M. M. Use of D-Ribonolactone in Organic Synthesis. 2. Scope and Utility. J. Org. Chem. 1984, 49, 2168-2176.
17. Cone, C.; Hough, L. A P.M.R. Study of the Conformation of Some Derivatives of Di-O-isopropylidene-arabinopyranose. Carbohydr. Res. 1965, 1, 1-9.
18. Bundle, D. R. Displacement of Sugar Chlorosulphates by Bromide, Azide, and Acetate: a Convenient Synthesis of Methyl 3,6-Dideoxy-β-D-ribo-hexopyranoside. J. Chem Soc., Perkin Trans. I 1979, 2751-2755.
19. Sheradsky, T. Azides as Synthetic Starting Materials. In The Chemistry of the Azido Group; Patai, S., Ed.; Interscience, New York, 1971, 333.
20. Marino, C.; Varela, O.; Lederkremer, R. M. Synthesis of Galactofuranose Dissacharides of Biological Significance. Carbohydr. Res. 1989, 190, 65-76.
21. Varela, O.; Marino, C.; Lederkremer, R. M. Synthesis of p-Nitrophenyl β-D-galactofuranoside. A Convenient Substrate for β-Galactofuranosidase. Carbohydr. Res. 1986, 155, 247-251.
22. Lewis, B. A.; Smith, F.; Stephen, A. M. 2,5- and 3,6-Anhydrosugars and their Derivatives. In Methods in Carbohydrate Chemistry, Vol II, Academic, New York, 1963, 174.
23. Hanessian, S. Sugar Lactams. III. Synthesis of Five-, Six-, and Seven-Membered Analogs. J. Org. Chem. 1969, 34, 675-681.
24. Green, J. W. Oxidative Reactions and Degradations. In The Carbohydrates, Chemistry and Biochemistry, Pigman, W. and Horton, D., Eds.; Vol IB, Academic, New York, 1980, 1142.
25. Bock, K.; Pedersen, C. Carbon-13 Nuclear Magnetic Resonance Spectroscopy of Monosaccharides. Adv. Carbohydr. Chem. Biochem. 1983, 41, 27-66.