Synthesis of C-disaccharides via a hetero-Diels-Alder reaction and further stereocontrolled transformations

Carbohydrate Research

Volumn 343, Issue 10-11, 2008, Pages 1754-1765

  Wan, Qian ^a   Lubineau, André ^a   Guillot, Régis ^a   Scherrmann, Marie Christine ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

C Glycoside; cis Dihydroxylation; d Glucosamine; Krapcho reaction

Indexed keywords

AMINES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

C-GLYCOSIDE; D-GLUCOSAMINE; KRAPCHO REACTION;

POLYSACCHARIDES;

GLUCOSAMINE; GLYCOSIDE;

ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CYCLOADDITION; DIELS ALDER REACTION; DIHYDROXYLATION; EPOXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY ANALYSIS;

CARBOHYDRATE CONFORMATION; DISACCHARIDES; STEREOISOMERISM;

ALNUS;

EID: 46549086404     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2008.03.015     Document Type: Article

References (61)

1. Reviews:. Postema M.H.D. C-Glycosides Synthesis (1995), CRC Press, Boca Raton
2. Levy D.E., and Tang C. The Chemistry of C-Glycosides (1995), Elsevier, Oxford
3. Beau J.-M., and Gallagher T. Top. Curr. Chem. 187 (1997) 1
4. Beau J.-M., Vauzeilles B., and Skrydstrup T. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience. Chemistry and Chemical Biology Vol. 3 (2001), Springer, Heidelberg 2679
5. For recent synthesis of C-disaccharides, see:. Stichler-Bonaparte J., and Vasella A. Helv. Chim. Acta 84 (2001) 2355-2367
6. Dondoni A., Marra A., Mamoru M., and Giovannini P.P. J. Org. Chem. 67 (2002) 4186-4199
7. Paterson D.E., Griffin F.K., Alcaraz M.-L., and Taylor R.J.K. Eur. J. Org. Chem. (2002) 1323-1326
8. Postema M.H.D., Piper J.L., Liu L., Shen J., Faust M., and Andreana P. J. Org. Chem. 68 (2003) 4748-4754
9. Mikkelsen L.M., and Skrydstrup T. J. Org. Chem. 68 (2003) 2123-2128
10. Kuberan B., Sikkander S.A., Tomiyama H., and Linhardt R.J. Angew. Chem., Int. Ed. 42 (2003) 2073-2075
11. Abdallah Z., Doisneau G., and Beau J.-M. Angew. Chem., Int. Ed. 42 (2003) 5209-5212
12. Dondoni A., and Marra A. Tetrahedron Lett. 44 (2003) 4067-4071
13. Demange R., Awad L., and Vogel P. Tetrahedron: Asymmetry 15 (2004) 3573-3585
14. Li X., Takahashi H., Ohtake H., and Ikegami S. Tetrahedron Lett. 45 (2004) 4123-4126
15. Chambers D.J., Evans G.R., and Fairbanks A.J. Tetrahedron 61 (2005) 7184-7192
16. Ress D.K., Baytas S.N., Wang Q., Munoz E.M., Tokuzoki K., Tomiyama H., and Lindhardt R.J. J. Org. Chem. 70 (2005) 8197-8200
17. Steunenberg P., Jeanneret V., Zhu Y.-H., and Vogel P. Tetrahedron: Asymmetry 16 (2005) 337-346
18. Cheshev P., Marra A., and Dondoni A. Org. Biomol. Chem. 4 (2006) 3225-3227
19. Ren Z.-X., Yang Q., Price K.N., Chen T., Nygren C., Turner J.F.C., and Baker D.C. Carbohydr. Res. 342 (2007) 1668-1679
20. Xin Y.-C., Zhang Y.-M., Mallet J.-M., Glaudemans C.P.J., and Sinaÿ P. Eur. J. Org. Chem. (1999) 471-476
21. Glaudemans C.P.J. Chem. Rev. 91 (1991) 25-33
22. Yang G., Schmieg J., Tsuji M., and Franck R.W. Angew. Chem., Int. Ed. 43 (2004) 3818-3822
23. Rodrigues F., Canac Y., and Lubineau A. Chem. Commun. (2000) 2049-2050
24. Hersant Y., Abou-Jneid R., Canac Y., Lubineau A., Philippe M., Semeria D., Radisson X., and Scherrmann M.-C. Carbohydr. Res. 339 (2004) 741-745
25. Bragnier N., and Scherrmann M.-C. Synthesis 5 (2005) 814-818
26. Canac Y., Levoirier E., and Lubineau A. J. Org. Chem. 66 (2001) 3206-3210
27. Lubineau A., Canac Y., and Le Goff N. Adv. Synth. Catal. 344 (2002) 319-327
28. Levoirier E., Canac Y., Norsikian S., and Lubineau A. Carbohydr. Res. 339 (2004) 2737-2747
29. Zeitouni J., Norsikian S., Merlet D., and Lubineau A. Adv. Synth. Catal. 348 (2006) 1662-1670
30. For a corrigendum, see:. Adv. Synth. Catal. 348 (2006) 2009
31. Dmitriev B.A., Knirel Y.A., and Kochetkov N.K. J. Biochem. 66 (1976) 559-566
32. Kovác P., and Edgar K.J. J. Org. Chem. 57 (1992) 2455-2467
33. Pozsgay V., and Coxon B. Carbohydr. Res. 277 (1995) 171-178
34. Pozsgay V. J. Org. Chem. 63 (1998) 5983-5999
35. Pozsgay V., Kubler-Kielb J., Schneerson R., and Robbins J.B. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 14478-14482
36. Wan Q., Lubineau A., and Scherrmann M.-C. J. Carbohydr. Chem. 23 (2004) 83-93
37. Ruden R.A., and Bonjouklian R. J. Am. Chem. Soc. 97 (1975) 6892-6893
38. Achmatowicz O., Jurczak J., and Pyrek J.S. Tetrahedron 32 (1976) 2113-2116
39. Bonjouklian R., and Ruden R.A. J. Org. Chem. 42 (1977) 4095-4103
40. Schmidt R., and Wagner A. Synthesis (1981) 273-275
41. Salomon R.G., Roy S., and Salomon M.F. Tetrahedron Lett. 29 (1988) 769-772
42. Robert H., Garrigues B., and Dubac J. Tetrahedron Lett. 39 (1998) 1161-1164
43. Yao S., Roberson M., Reichel F., Hazell R.G., and Jørgensen K.A. J. Org. Chem. 64 (1999) 6677-6687
44. David S., Eustache J., and Lubineau A. J. Chem. Soc., Perkin Trans. 1 (1979) 1795-1798
45. Knapp S., Levorse A.T., and Potenza J.A. J. Org. Chem. 53 (1988) 4773-4779
46. Bataille C., Bégin G., Guillam A., Lemiègre L., Lys C., Maddaluno J., and Toupet L. J. Org. Chem. 67 (2002) 8054-8062
47. Krapcho A.P. Synthesis 805 (1982) 893-914
48. Sharpless K.B., and Lauer R.F. J. Am. Chem. Soc. 95 (1973) 2697-2699
49. O'Brien P. J. Chem. Soc., Perkin Trans. 1 (1998) 1439-1457
50. Inoue T., Uchimaru T., and Mukaiyama T. Chem. Lett. (1977) 1215-1218
51. Detty M.R. J. Org. Chem. 45 (1980) 924-926
52. Murata S., Suzuki M., and Noyori R. J. Am. Chem. Soc. 101 (1979) 2738-2739
53. Murata S., Suzuki M., and Noyori R. Bull. Chem. Soc. Jpn. 55 (1982) 247-254
54. Mosset P., Mana S., Viala J., and Falk J.R. Tetrahedron Lett. 27 (1986) 299-302
55. Cha J.K., Christ W.J., and Kishi Y. Tetrahedron Lett. 24 (1983) 3943-3946
56. Christ W.J., Cha J.K., and Kishi Y. Tetrahedron Lett. 24 (1983) 3947-3950
57. Cha J.K., Christ W.J., and Kishi Y. Tetrahedron 40 (1984) 2247-2255
58. For a review see:. Cha J.K., and Kim N.S. Chem. Rev. 95 (1995) 1761-1795
59. Sheldrick, G. M. shelxs-97, Program for Crystal Structure Solution, University of Göttingen, Göttingen, Germany, 1997.
60. Sheldrick, G. M. shelxl-97, Program for the refinement of crystal structures from diffraction data, University of Göttingen, Göttingen, Germany, 1997.
61. Farrugia L.J. J. Appl. Crystallogr. 32 (1999) 837-838