Selective cleavage of methoxy protecting groups in carbohydrates

Journal of Organic Chemistry

Volumn 71, Issue 5, 2006, Pages 1938-1948

  Boto, Alicia ^a   Hernández, Dácil ^a   Hernández, Rosendo ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ABSTRACTION REACTION; HYDROGEN ABSTRACTION; SENSITIVE SUBSTRATES;

HYDROGEN; HYDROLYSIS; REACTION KINETICS; SUBSTRATES; SULFUR COMPOUNDS;

CARBOHYDRATES;

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; CARBOHYDRATE; GALACTOSE; GLUCOSE; HYDROGEN; RADICAL; RHAMNOSE; XYLOSE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DISSOCIATION; HYDROLYSIS; INFRARED SPECTROSCOPY; INTRAMOLECULAR HYDROGEN ABSTRACTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ACETALS; ACETATES; CARBOHYDRATES; GALACTOSE; GLUCOSE; HYDROGEN; HYDROLYSIS;

EID: 33644652147     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052313o     Document Type: Article

References (53)

1. (a) For a recent review on ether dealkylation, see: Weissman, S. A.; Zewge, D. Tetrahedron 2005, 61, 7833-7863.
2. (b) See also: Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley & Sons: New York, 1999.
3. For a previous communication on this work, see: Boto, A.; Hernández, D.; Hernández, R.; Suárez, E. Org. Lett. 2004, 6, 3785-3788.
4. Schmidt, O. T. Methods Carbohydr. Chem. 1963, 2, 318-325.
5. Mariño-Albernas, J. R.; Verez-Bencomo, V.; Gonzalez, L.; Perez, C. S. Carbohydr. Res. 1987, 165, 197-206.
6. Parr, I. B.; Horenstein, B. A. J. Org. Chem. 1997, 62, 7489-7494.
7. Laidlaw, R. A. J. Chem. Soc. 1952, 2941-2943.
8. Sharma, G. V. M.; Reddy, V. G.; Krisha, P. R. Tetrahedron: Asymmetry 1999, 10, 3777-3784.
9. Vries, N. K.; Buck, H. M. Carbohydr. Res. 1987, 165, 1-16.
10. For other similar epimerizations, see: Lee, C. K.; Kim, E. J.; Lee, I.-S. H. Carbohydr. Res. 1998, 309, 243-250.
11. (a) Smith, F. J. Chem. Soc. 1939, 1724-1730.
12. See also: (b) Van Langenhove, A.; Reinhold, V. N. Carbohydr. Res. 1985, 143, 1-20.
13. (a) Krohn, K.; Börner, G.; Gringard, S. J. Org. Chem. 1994, 59, 6066-6074.
14. (b) Francisco, C. G.; González, C. C.; Suárez, E. J. Org. Chem. 1998, 63, 2099-2109.
15. (a) For the permethylation of sugars, see: Wang, H.; Sun, L.; Glazebnik, S.; Zhao, K. Tetrahedron Lett. 1995, 36, 2953-2956.
16. (b) Aspinall, G. O.; Capek, P.; Carpenter, R. C.; Szafranek, J. Carbohydr. Res. 1991, 214, 95-105.
17. Reuben, J. Carbohydr. Res. 1986, 157, 201-213.
18. Cesane, P. D.; Duchaussoy, P.; Gross, B. Synthesis 1980, 953-954.
19. (a) Hirooka, M.; Koto, S. Bull. Chem. Soc. Jpn. 1998, 71, 2893-2902.
20. (b) For a route in which product 30 is obtained from octaacetyl D-malthose, see: Maillard, P.; Guerquin-Kern, J.-L.; Huel, C.; Momenteau, M. J. Org. Chem. 1993, 58, 2774-2780.
21. (c) Bhaskar, P. M.; Loganathan, D. Synlett 1999, 129-131.
22. (d) Twaddle, G. W. J.; Yashunsky, D. V.; Nikolaev, A. V. Org. Biomol. Chem. 2003, 1, 623-628.
23. (a) Lipták, A.; Nánási, P.; Neszmélyi, A.; Wagner, H. Tetrahedron 1980, 36, 1261-1268.
24. (b) Gound, S.; Langer, H.-J.; Henne, P.; Sattler, I.; Triericke, R.; Grabley, S.; Zähner, H.; Zeck, A. Eur. J. Org. Chem. 2000, 929-937.
25. Harangi, J.; Lipták, A.; Olah, V. A.; Nánási, P. Carbohydr. Res. 1981, 98, 165-171.
26. Haykó, J.; Borbás, A.; Szabovik, G.; Kajtár-Peredy, M.; Lipták, A. J. Carbohydr. Chem. 1997, 16, 1123-1144.
27. Hong, N.; Funabashi, M.; Yoshimura, J. Carbohydr. Res. 1981, 96, 21-28.
28. (a) Toman, R.; Karácsonyi, S.; Palovcík, R. Carbohydr. Res. 1977, 56, 191-194.
29. (b) Monneret, C.; Gagnet, R.; Florent, J. C. Carbohydr. Res. 1987, 6, 221-229.
30. Boto, A.; Hernández, D.; Hernández, R.; Suárez, E. J. Org. Chem. 2003, 68, 5310-5319.
31. (a) For reviews on hydrogen abstraction, see: Cekovic, Z. Tetrahedron 2003, 59, 8073-8090.
32. (b) Feray, L.; Kuznetsov, N.; Renaud, P. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 246-278.
33. (c) Robertson, J.; Pillai, J.; Lush. R. K. Chem. Soc. Rev. 2001, 30, 94-103 and references therein.
34. 13C NMR, MS, HRMS, IR, and elemental analysis. 2D-COSY, HSQC, and NOESY experiments were also carried out.
35. For reviews on β-fragmentation, see: (a) Hartung, J.; Gottwald, T.; Spehar, K. Synthesis 2002, 1469-1498.
36. (b) Zhdankin, V.; Stang, P. J. Chem. Rev. 2002, 102, 2523-2584.
37. (c) Togo, H.; Katohgi, M. Synlett 2001, 565-581.
38. (d) Zhang, W. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 234-245.
39. (e) Suárez, E.; Rodríguez, M. S. In Radicals in Organic Synthesis; Renaud. P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 440-454.
40. (f) McCarroll, A. J.; Walton, J. C. Angew. Chem., Int. Ed. 2001, 40, 2224-2248 and references therein.
41. For related work, see: de Armas, P.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1989, 405-411.
42. (a) Binkley, R. W.; Koholic, D. J. J. Carbohydr. Chem. 1984, 3, 85-106.
43. (b) Binkley, R. W.; Koholic, D. J. J. Org. Chem. 1979, 44, 2047-2048.
44. (a) Calculations were made using an AMBER force field model implanted in the Macromodel 7.0 program. The calculations were also performed with an MMFF force field, using high-quality parameters. Similar results were obtained in both cases.
45. (b) For more information on this software, see: Mohamadi, F.; Richard, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrikson, T.; Stille, W. C. J. Comput. Chem. 1990, 11, 440.
46. (a) For other related works, see: Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2002, 67, 7439-7445.
47. (b) Francisco, C. G.; Freire, R.; Herrera, A. J.; Pérez- Martín, I.; Suárez, E. Org. Lett. 2002, 11, 1959-1961.
48. (c) Madsen, J.; Viuf, C.; Bols, M. Chem.-Eur. J. 2000, 6, 1140-1146.
49. (d) Francisco, C. G.; Herrera, A. J.; Suárez, E. Tetrahedron Lett. 2000, 41, 7869-7873.
50. The IHA examples suggest that the formation of O-methyl acetates predominates over the generation of five-membered dioxolane rings. On the contrary, the formation of six-membered methylenedioxy acetals between the C-4 and C-6 positions is favored over the generation of O-methyl acetates.
51. Shasma, B. S.; Doane, W. M. Carbohydr. Res. 1974, 34, 370-375.
52. Gras, J. L.; Pellissier, H.; Nouguier, R. J. Org. Chem. 1989, 54, 5675-5677.
53. Evtushenko, E. V. Carbohydr. Res. 1999, 316, 187-200.