4-AcNH-tempo-catalyzed oxidation of aldoses to aldaric acids using chlorine or bromine as terminal oxidants

Journal of Carbohydrate Chemistry

Volumn 21, Issue 1-2, 2002, Pages 65-77

  Merbouh, Nabyl ^a   Bobbitt, James M ^a   Brückner, Christian ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETYLAMINO 2,2,6,6 TETRAMETHYL 1 PIPERIDINYLOXY; BROMINE; CARBOHYDRATE DERIVATIVE; CHLORINE; GALACTOSE; GLUCOSE; MANNARIC ACID; MANNOSE; MONOPOTASSIUM DEXTRO GLUCARATE; MUCIC ACID; OXIDIZING AGENT; PIPERIDINE DERIVATIVE; SACCHARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CRYSTALLIZATION; OXIDATION; PH; PRECIPITATION; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; TEMPERATURE;

EID: 0035998777     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-120003738     Document Type: Article

References (58)

1. Lichtenthaler, F.W. Carbohydrates as Organic Raw Materials; VCH: Weinheim, 1991.
2. Thiem, J.; Bachmann, F. Carbohydrate-derived polyamides. Trends Polym. Sci. 1994, 2 (12), 425-432.
3. Gonsalves, K.E.; Mungara, P.M. Synthesis and properties of degradable polyamides and related polymers. Trends Polym. Sci. 1996, 4 (1), 25-31.
4. Mohanty, A.K.; Misra, M.; Hinrichsen, G. Biofibres, biodegradable polymers and biocomposites. Macromol. Mater. Eng. 2000, 276/277, 1-24.
5. Röper, H. Selective Oxidation of D-Glucose: Chiral Intermediates for Industrial Utilization. In Carbohydrates as Organic Raw Materials; F.W. Lichtenthaler, Ed.; VCH: Weinheim, 1991; pp. 267-288.
6. Kiely, D.E. Carbohydrate Diacids: Potential as Commercial Chemicals and Hydrophilic Polyamide Precursors. Book of Abstracts, 218th National Meeting of the American Chemical Society, New Orleans, LA, Aug. 22-26, 1999, American Chemical Society: Washington, DC, 1999; CELL-016.
7. Dijkgraaf, P.J.M.; Verkuylen, M.E.C.G.; Van der Wiele, K. Complexation of calcium ions by complexes of glucaric acid and boric acid. Carbohydr. Res. 1987, 163 (1), 127-131.
8. Kiely, D.E.; Chen, L.; Lin, T.H. Hydroxylated nylons based on unprotected esterified D-glucaric acid by simple condensation reactions. J. Am. Chem. Soc. 1994, 116 (2), 571-578.
9. Chen, L.; Kiely, D.E. D-Glucaric acid esters/lactones used in condensation polymerization to produce hydroxylated nylons-a qualitative equilibrium study in acidic and basic alcohol solutions. J. Carbohydr. Chem. 1994, 13 (4), 585-601.
10. Kiely, D.E.; Chen, 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 (3), 594-603.
11. Chen, L.; Kiely, D.E. Synthesis of stereoregular head-tail hydroxylated nylons derived from D-glucose. J. Org. Chem. 1996, 61 (17), 5847-5851.
12. Abou-Issa, H.; Koolemans-Beynen, A.; Minton, J.P.; Webb, T.E. Synergistic interaction between 13-cis-retinoic acid and glucarate: activity against rat mammary tumor induction and MCF-7 Cells. Biochem. Biophys. Res. Commun. 1989, 163 (3), 1364-1369.
13. Abou-Issa, H.; Dwivedi, C.; Curley, R.W., Jr.; El-Masry, W.; Webb, T.E. Basis for the antitumor and chemopreventive activities of glucarate and the glucarate-retinoid combination. Anticancer Res. 1993, 13 (2), 395-399.
14. Steele, V.E.; Moon, R.C.; Lubet, R.A.; Grubbs, C.J.; Reddy, B.S.; Wargovich, M.; McCormick, D.L.; Pereira, M.A.; Crowell, J.A. Preclinical evaluation of potential chemopreventive agents in animal carcinogenesis model: methods and results from the NCI chemoprevention drug development program. J. Cell. Biochem. 1994, (Suppl. 20), 32-54.
15. Walaszek, Z.; Szemraj, J.; Hanausek, M.; Adams, A.K.; Sherman, U. D-Glucaric acid content of various fruits and vegetables and cholesterol-lowering effects of dietary D-glucarate in rats. Nutr. Res. (N.Y.) 1996, 16 (4), 673-681.
16. 99mTc-glucaratefs. Nucl. Med. Commun. 1997, 18 (3), 241-251.
17. 99mTc glucarate. Circulation 1997, 95 (6), 1577-1584.
18. Pamuk, V.; Yilmaz, M.; Alicilar, A. The preparation of D-glucaric acid by oxidation of molasses in packed beds. J. Chem. Technol. Biotechnol. 2001, 76, 186-190.
19. Maurer, K.; Drehfal, G. Oxidation mit Stickstoffdioxyd, I. Mitteil.: Die Darstellung von Glyoxylsäure, Glucoronsäure und Galakturonsäure. Chem. Ber. 1942, 75, 1489-1491.
20. Mehltretter, C.L.; Rist, C.E. Saccharic and oxalic acid by the nitric acid oxidation of dextrose. J. Agric. Food Chem. 1953, 1 (12), 779-783.
21. Mehltretter, C.L. D-Glucaric Acid. In Methods in Carbohydrate Chemistry; Whistler, R.L.; Wolfrom, M.L., Eds.; Academic Press: New York, 1962; Vol. II, pp. 46-48.
22. Rakovsky, S.K.; Sheldon, R.A.; v. Rantwijk, F. Carbohydrate ozonation. Selective cleavage of the 2,3 C-C bond in carbohydrates. Oxidation Commun. 1996, 19 (4), 482-498.
23. Kiely, D.E.; Ponder, G. Extraction Method for the Removal of Residual Nitric Acid from Oxidation Products. US Patent 6,049,004, April 11, 2000.
24. Kiely, D.; Carter, A.; Shrout, D. Improved Oxidation Process. US Patent 5,599,977, February 4, 1996.
25. Mehltretter, C.L., Rist, C.E. D-Glucosaccharic Acid. US Patent 2472168, June 7, 1949.
26. Floor, M.; Schenk, K.M.; Kieboom, A.P.G.; van Bekkum, H. Oxidation of maltodextrin and starch by the system tungstate-hydrogen peroxide. Starch/Stärke 1989, 41 (8), 303-309.
27. van Dam, H.E.; Wisse, L.J.; van Bekkum, H. Platinum/carbon oxidation catalysts. Appl. Catal. 1990, 61, 187-197.
28. Anelli, P.L.; Banfi, S.; Montanari, F.; Quici, S. Oxidation of diols with alkali hypochlorites catalyzed by oxoammonium salts under two-phase conditions. J. Org. Chem. 1989, 54 (12), 2970-2972.
29. Bobbitt, J.M. Oxoammonium Salts. 6. 4-acetylamino-2,2,6,6-tetramethylpiperidine perchlorate: a stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis. J. Org. Chem. 1998, 63 (25), 9367-9375.
30. Bolm, C.; Magnus, A.S.; Hildebrand, J.P. Catalytic synthesis of aldehydes and kerones under mild conditions using TEMPO/oxone. Chem. Lett. 2000, 2 (8), 1173-1175.
31. Bobbitt, J.M.; Flores, C.L. Organic nitrosonium salts as oxidants in organic chemistry. Heterocycles 1988, 27, 509-533.
32. de Nooy, A.E.J.; Besemer, A.C.; van Bekkum, H. On the use of stable organic nitroxyl radicals for the oxidation of primary and secondary alcohols. Synthesis 1996, 10, 1153-1175.
33. Davis, N.J.; Flitsch, S.L. Selective oxidation of monosaccharide derivatives to uronic acids. Tetrahedron Lett. 1993, 34, 1181-1184.
34. de Nooy, A.E.J.; Besemer, A.C.; van Bekkum, H. Highly selective TEMPO mediated oxidation of primary alcohol groups in polysaccharides. Recl. Trav. Chim. Pays-Bas 1994, 113 (3), 165-166.
35. de Nooy, A.E.J.; Besemer, A.C.; van Bekkum, H. Highly selective nitrosyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans. Carbohydr. Res. 1995, 269 (1), 89-98.
36. de Nooy, A.E.J.; Besemer, A.C.; van Bekkum, H.; van Dijk, J.A.P.P.; Smit, J.A.M. TEMPO-mediated oxidation of pullulan and influence of ionic strength and linear charge density on the dimensions of the obtained polyelectrolyte chains. Macro-molecules 1996, 29 (20), 6541-6547.
37. Chang, P.S.; Robyt, J.F. Oxidation of primary alcohol groups of naturally occurring polysaccharides with 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion. J. Carbohydr. Chem. 1996, 15 (7), 819-830.
38. Chang, P.S.; Robyt, J.F. Oxidation of the primary alcohol groups of cyclomaltodextrins with 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion. Carbohydr. Lett. 1998, 3 (1), 31-38.
39. Thaburet, J.F.; Merbouh, N.; Ibert, M.; Marsais, F.; Queguiner, G. TEMPO-mediated oxidation of maltodextrines and D-glucose: effect of pH on the selectivity and sequestering ability of the resulting polycarboxylates. Carbohydr. Res. 2001, 330 (1), 21-29.
40. Weik, S.; Nicholson, G.; Jung, G.; Rademann, J. Oxoammonium resins as metal free, highly reactive, versatile polymeric oxidation reagents. Angew. Chem. Int. Ed. Engl. 2001, 40 (8), 1436-1439.
41. Bolm, C.; Fey, T. TEMPO oxidations with a silica-supported catalyst. Chem. Commun. 1999, 1795-1796.
42. Merbouh, N.; Thaburet, J.F.; Ibert, M.; Marsais, F.; Bobbitt, J.M. Facile nitroxide-mediated oxidation of D-glucose to D-glucaric acid. Carbohydr. Res. 2001, 336, 75-78.
43. Schmeisser, M. In Handbook of Preparative Inorganic Chemsitry; G. Brauer, Ed.; Academic Press: New York, 1963; Vol. 1, pp. 308-311.
44. The oxidation of reducing sugars with iodine in alkaline media is known (see e.g. M.K. Singh, N. Prasad, H.K. Sinha, Asian J. Chem. 1994, 6, 636-640 and references therein.) However, we have not tested iodine in the nitroxide-mediated oxidations as iodine is not known to oxidize the nitroxide to the corresponding nitroxonium salt.
45. Bose, R.J.; Hullar, T.L.; Lewis, B.A.; Smith, F. Isolation of the 1,4- and 6,3-lactones of D-glucaric acid. J. Org. Chem. 1961, 26, 1300-1301.
46. Smith, F. Lactones of glucossacharic acid. (Part III). J. Chem. Soc. 1944, 571, 633-636.
47. The NMR corresponds to none of the likely decomposition products such as those listed in Ref. 57.
48. Solomon, K.R. Chlorine in the leaching of pulp and paper. Pure Appl. Chem. 1996, 68 (9), 1721-1730.
49. Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tsahen, D.M.; Grabowski, E.J.J.; Reider, P. Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalysed by TEMPO and bleach. J. Org. Chem. 1999, 64 (7), 2564-2566.
50. Giddings, S.; Mills, A. Optimization of a simple system for the oxidaton octan-2-ol with sodium bromate. Mediated by ruthenium tetroxide generated in situ. J. Org. Chem. 1988, 53 (5), 1103-1107.
51. de Nooy, A.E.J.; Besemer, A.C.; van Bekkum, H. Selective oxidation of primary alcohols mediated by nitroxyl radical in aqueous solution. Kinetics and mechanism. Tetrahedron 1995, 51 (29), 8023-8032.
52. Rychnovsky, S.D.; Vaidyanathan, R. TEMPO-catalyzed oxidations of alcohols using m-CPBA: the role of halide ions. J. Org. Chem. 1999, 64, 310-312.
53. Yamaguchi, M.; Takata, T.; Endo, T. Oxidation of cycloalkanols to the corresponding cycloalkanones with chlorine in the presence of nitroxide radical as a mediator. Bull. Chem. Soc. Jpn. 1990, 63 (3), 947-949.
54. Mohrig, J.R.; Nienhuis, D.M.; Linck, C.F.; Van Zoeren, C.; Fox, B.G.; Mahaffy, P.G. A case study on the oxidation of alcohols with household bleach. J. Chem. Educ. 1985, 62 (6), 519-521.
55. Whistler, R.L.; Schweiger, R. Preparation of D-arabinose from D-glucose with hypochlorite. J. Am. Chem. Soc. 1959, 81, 5190-5192.
56. Whistler, R.L.; Yagi, K. Further application of the hypochlorite methods of chain shortening in the carbohydrate series. J. Org. Chem. 1961, 26, 1050-1052.
57. van Duin, M.; Peters, J.A.; Kieboom, A.P.G.; van Bekkum, H. Proton NMR spectra of carbohydrate-derived polyhydroxycarboxylates. Magn. Reson. Chem. 1986, 24 (9), 832-833.
58. Merbouh, N.; Bobbitt, J.M.; Brückner, C. U.S. Patent Application 09/690, 614, October 17, 2000.