Highly stereoselective synthesis of 2-amino-3-c-methyl-2,3-dideoxyaldoses by C3-chain elongation via homoaldol reaction of sugar aldehydes

Synthesis

Volumn , Issue 5, 2010, Pages 749-756

  Kollmann, Sabine ^a   Fröhlich, Roland ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aminoaldoses; Carbamates; Furanosides; Homoaldol reaction; Stereoselective synthesis

Indexed keywords

AMINO SUGAR; BROAD APPLICATION; CHAIN ELONGATION; DIASTEREOSELECTIVITIES; FLEXIBLE STRATEGIES; HIGH YIELD; HOMOALDOL REACTIONS; METHANOLYSIS; STEREOSELECTIVE SYNTHESIS; TITLE COMPOUNDS; TRIFLATES;

ALDEHYDES; AMINATION; AMINES; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

2 AMINO 3 METHYL 2,3 DIDEOXYALDOSE DERIVATIVE; ALDEHYDE; ALPHA METHYLALLOFURANOSIDE; AMINOSUGAR; ARABINOSE; CARBAMIC ACID; GLYCOSIDE; KETONE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; AMINATION; ARTICLE; EPOXIDATION; METHANOLYSIS; STEREOCHEMISTRY;

EID: 77955352103     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/S-0029-1218628     Document Type: Article

References (69)

1. X-ray crystal structure analysis.
2. (a) Tang, P.; Mamdani, F.; Hu, X.; Liu, J. O.; Yu, B. Bioorg. Med. Chem. Lett. 2007, 17, 1003.
3. (b) Ferrier, R. J. Carbohydr. Chem. 2003, 34, 166.
4. (c) Gravier-Pelletier, C.; Milla, M.; Le Merrer, Y.; Depezay, J.-C. Eur. J. Org. Chem. 2001, 3089.
5. Selected examples: (a) Zhang, C.; Fu, Q.; Albermann, C.; Li, L.; Thorson, J. S. ChemBioChem 2007, 8, 385.
6. (b) Hanessian, S.; Kloss, J. Tetrahedron Lett. 1985, 26, 1261.
7. (c) Sarabia, F.; Martin-Ortiz, L.; Lopez-Herrera, F. J. Org. Lett. 2003, 5, 3927.
8. Selected examples: (a) Anizon, F.; Belin, L.; Moreau, P.; Sancelme, M.; Voldoire, A.; Prudhomme, M.; Oilier, M.; Sevère, D.; Riou, J.-F.; Bailly, C.; Fabbro, D.; Meyer, T. J. Med. Chem. 1997, 40, 3456.
9. (b) El-Hamamsy, M. H. R. I.; Smith, A. W.; Thompson, A. S.; Threadgill, M. D. Bioorg. Med. Chem. 2007, 15, 4552.
10. Selected examples: (a) Zhang, C.; Griffith, B. R.; Fu, Q.; Albermann, C.; Fu, X.; Lee, I.-K.; Li, L.; Thorson, J. S. Science 2006, 313, 1291.
11. (b) Ahmed, S. A.; Odde, S.; Daga, P. R.; Bowling, J. J.; Mesbah, M. K.; Youssef, D. T.; Khalifa, S. I.; Doerksen, R. J.; Hamann, M. T. Org. Lett. 2007, 9, 4773.
12. (a) Pfrengle, F.; Lentz, D.; Reißig, H.-U. Angew. Chem. Int. Ed. 2009, 48, 3165
13. Angew. Chem 2009, 121, 3211.
14. (b) Ferrier, R. J. Carbohydr. Chem. 2003, 34, 175.
15. (c) Ferrier, R. J. Carbohydr. Chem. 2003, 34, 118.
16. (d) Nicolaou, K. C.; Chem, J. S.; Edmonds, R. J.; Estrada, A. A. Angew. Chem. Int. Ed. 2009, 48, 660
17. Angew. Chem. 2009, 121, 670.
18. (e) Westermann, B.; Neuhaus, C. Angew. Chem. Int. Ed. 2005, 46, 4077
19. Angew. Chem. 2005, 117, 4145.
20. (f) Enders, D.; Grondal, G.; Vretton, M.; Raabe, G. Angew. Chem. Int. Ed. 2005, 44, 4079
21. Angew. Chem. 2005, 117, 4147.
22. A research in Scifinder afforded no hit.
23. Hoppe, D.; Hanko, R.; Brönneke, A.; Lichtenberg, F.; van Hülsen, E. Chem. Ber. 1985, 118, 2822.
24. For reviews, see: (a) Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282
25. Angew. Chem. 1997, 109, 2376.
26. (b) Hoppe, D.; Marr, F.; Brüggemann, M. Top. Organomet. Chem. 2003, 5, 61.
27. (c) Christoph, G.; Hoppe, D. In The Chemistry of Organolithium Compounds; Rappoport, Z.; Marek, I., Eds.; Wiley: Chichester, 2004, 1055.
28. (d) Hoppe, D. Synthesis 2009, 43.
29. (a) Hoppe, D.; Zschage, O. Angew. Chem. Int. Ed. 1989, 26, 69
30. Angew. Chem. 1989, 101, 67.
31. (b) Paulsen, H.; Graeve, C.; Hoppe, D. Synthesis 1996, 141.
32. (a) Tipson, R. S.; Cohen, A. Carbohydr. Res. 1968, 7, 232.
33. (b) Jackson, D. Y. Synth. Commun. 1988, 18, 337.
34. (c) Schmidt, O. T. Methods Carbohydr. Chem. 1963, 2, 318.
35. (d) Czernecki, S.; Dieulesaint, A.; Valery, J.-M. J. Carbohydr. Chem. 1986, 5, 469.
36. (e) Szarek, M. A.; Wu, X.; Szarek, W. A. Carbohydr. Res. 1997, 299, 165.
37. (f) Swern, D. J. Org. Chem. 1978, 43, 2480.
38. (g) Redlich, H.; Kölln, O. Synthesis 1995, 1376.
39. (h) Leonard, N. J.; Carraway, K. L. J. Heterocycl. Chem. 1966, 3, 485.
40. (i) Fernandes, R. A. Eur. J. Org. Chem. 2007, 5064; and references cited therein.
41. Kollmann, S.; Fröhlich, R.; Hoppe, D. Synthesis 2007, 883.
42. (a) Hoppe, D.; Lußmann, J.; Jones, P. G.; Schmidt, D.; Sheldrick, G. M. Tetrahedron Lett. 1986, 27, 3591.
43. (b) Sharpless, K. B.; Verhoeven, T. Aldrichimica Acta 1979, 12, 63.
44. (c) Wang, Z.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 31.
45. (d) Torres, G.; Torres, W.; Prieto, J. A. Tetrahedron 2004, 60, 10245.
46. (e) Ohshima, T. Chem. Pharm. Bull. 2004, 52, 1031.
47. For reviews see: (f) Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2024
48. Angew. Chem. 2002, 114, 2126.
49. (g) Sharpless, K. B.; Johnson, R. A. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, 231.
50. (h) Marco-Contelles, L.; Molina, M. T.; Anjum, S. Chem. Rev. 2004, 104, 2857.
51. (i) Katsuki, T. Curr. Org. Chem. 2001, 5, 663.
52. Hoppe, D.; Tarara, G.; Wilckens, M. Synthesis 1989, 83.
53. Ünaldi, S.; Frohlich, R.; Hoppe, D. Synthesis 2005, 2507.
54. -3, hydrogen atoms calculated and refined as riding atoms.
55. 23
56. COLLECT, Nonius B. V.: Delft, 1998.
57. Otwinowski, Z.; Minor, W. Methods in Enzymology: Macromolecular Crystallography, Part A, 276; Carter, C. W. Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997, 307-326.
58. Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr., Sect. A 2003, 59, 228.
59. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467.
60. Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.
61. Brüggemann, M. Mopict; Universität Münster: Münster, 2001.
62. CCDC 747428 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223) 336033, E-mail: deposit@ccdc.cam.ac. uk].
63. (a) Binkley, R. M.; Ambrose, M. G. J. Carbohydr. Res. 1984, 3, 1.
64. (b) Review: Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85.
65. (a) Fuchs, W.; Voelter, W. Liebigs Ann. Chem. 1982, 1920.
66. (b) Hanessian, S. Preparative Carbohydrate Chemistry; Marcel Decker: New York, 1997.
67. (a) Corey, E. J.; Nicolaou, K. C.; Balanson, R. D.; Machida, Y. Synthesis 1975, 590.
68. (b) Reddy, P. G.; Pratap, T. V.; Kumar, G. D. K.; Mohanty, S. K.; Baskaran, S. Eur. J. Org. Chem. 2002, 3740.
69. Dearden, M. J.; Firkin, C. R.; Hermet, J.-P.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870.