A practical fluorous benzylidene acetal protecting group for a quick synthesis of disaccharides

Tetrahedron Letters

Volumn 48, Issue 25, 2007, Pages 4431-4436

  Kojima, Masaru ^a   Nakamura, Yutaka ^a   Takeuchi, Seiji ^a  

^a NIIGATA UNIVERSITY OF PHARMACY AND APPLIED LIFE SCIENCES   (Japan)

Author keywords

Benzylidene acetal group; Fluorous solid phase extraction; Oligosacchrides; Regioselective reduction

Indexed keywords

ACETAL DERIVATIVE; CARBOHYDRATE; FLUOROUS BENZYLIDENE ACETAL; OLIGOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 34248650137     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.106     Document Type: Article

References (67)

1. Zhang W. The Handbook of Fluorous Chemistry. In: Gladys J.A., Curran D.P., and Horváth I.T. (Eds) (2004), Wiley-VCH, Weinheim 222-235
2. For reviews on FSPE, see:. Zhang W., and Curran D.P. Tetrahedron 62 (2006) 11837-11865
3. Curran D.P. In: Gladys J.A., Curran D.P., and Horváth I.T. (Eds). The Handbook of Fluorous Chemistry (2004), Wiley-VCH, Weinheim 101-127
4. Curran D.P. Synlett (2001) 1488-1496
5. Curran D.P., Ferritto R., and Hua Y. Tetrahedron Lett. 39 (1998) 4937-4940
6. Wipf P., and Reeves J.T. Tetrahedron Lett. 40 (1999) 4649-4652
7. Röver S., and Wipf P. Tetrahedron Lett. 40 (1999) 5667-5670
8. Curran D.P., Ferritto R., and Hua Y. Tetrahedron Lett. 39 (1998) 4937-4940
9. Manzoni L., and Castelli R. Org. Lett. 6 (2004) 4195-4198
10. Curran D.P., and Ogoe C. QSAR Comb. Sci. 8 (2006) 732-735
11. Filippov V., van Zoelen D.J., Oldfield S.P., van der Marel G.A., Overkleeft H.S., Drijfhout J.W., and van Boom J.H. Tetrahedron Lett. 43 (2002) 7809-7819
12. Schwinn D., and Bannwarth W. Helv. Chim. Acta 85 (2002) 255-264
13. Luo Z.Y., Williams J., Read R.W., and Curran D.P. J. Org. Chem. 66 (2001) 4261-4266
14. Curran D.P., Amatore M., Guthrie D., Campbel M., Go E., and Luo Z. J. Org. Chem. 68 (2003) 4643-4647
15. Matsugi M., Yamanaka K., Inomata I., Takekoshi N., Hasegawa M., and Curran D.P. QSAR Comb. Sci. 8 (2006) 713-715
16. Pardo J., Cobas A., Guitián E., and Castedo L. Org. Lett. 23 (2001) 3711-3714
17. Fustero S., Sancho A.G., Chiva G., Sanz-Cervera J.F., del Pozo C., and Aceña J.L. J. Org. Chem. 71 (2006) 3299-3302
18. Huang Y., and Qing F.-L. Tetrahedron 60 (2004) 8341-8346
19. Read R.W., and Zhang C. Tetrahedron Lett. 44 (2003) 7045-7047
20. Schwinn D., and Bannwarth W. Helv. Chim. Acta 85 (2002) 255-264
21. Miura T., Hirose Y., Ohmae M., and Inazu T. Org. Lett. 3 (2001) 3947-3950
22. Miura T., and Inazu T. Tetrahedron Lett. 44 (2003) 1819-1821
23. Mizuno M., Goto K., Miura T., Hosaka D., and Inazu T. Chem. Commun. (2003) 972-973
24. Miura T., Goto K., Hosaka D., and Inazu T. Angew. Chem., Int. Ed. 42 (2003) 2047-2051
25. Mizuno M., Goto K., Miura T., Matsuura T., and Inazu T. Tetrahedron Lett. 45 (2004) 3425-3428
26. Miura T., Satoh A., Goto K., Muratami Y., Imai N., and Inazu T. Tetrahedron: Asymmetry 16 (2005) 3-6
27. Manzoni L., and Castelli R. Org. Lett. 8 (2006) 955-957
28. Goto K., Miura T., and Mizuno M. Tetrahedron Lett. 46 (2005) 8293-8297
29. Mizuno M., Goto K., and Miura T. Chem. Lett. 34 (2005) 426-427
30. Person W.H., Berry D.A., Stoy P., Jung K., and Sercel A.D. J. Org. Chem. 70 (2005) 7114-7122
31. Beller C., and Bannwarth W. Helv. Chim. Acta 88 (2005) 171-179
32. Nakamura Y., Okumura K., Kojima M., and Takeuchi S. Tetrahedron Lett. 47 (2006) 239-243
33. Mizuno M., Matsumoto H., Goto K., and Hamasaki K. Tetrahedron Lett. 47 (2006) 8831-8835
34. Ikeda K., Mori H., and Sato M. Chem. Commun. (2006) 3093-3094
35. Kojima M., Nakamura Y., Ishikawa T., and Takeuchi S. Tetrahedron Lett. 47 (2006) 6309-6314
36. Wuts P.G.M., and Greene T.W. Greene's Protective Groups in Organic Synthesis. 4th ed. (2006), John Wiley and Sons
37. Chrétien F., Khaldi M., and Chapleur Y. Synth. Commun. 20 (1990) 1589-1596
38. Sato K., Igarashi T., Yanagisawa Y., Kawauchi N., Hashimoto H., and Yoshimura J. Chem. Lett. (1988) 1699-1702
39. DeNinno M.P., Etienne J.B., and Duplantier K.C. Tetrahedron Lett. 36 (1995) 669-672
40. Sakagami M., and Hamana H. Tetrahedron Lett. 41 (2000) 5547-5551
41. Shie C.-R., Toone Z.-H., Kulkarni S.S., Uang B.-J., Hsu C.-Y., and Hung S.-C. Angew. Chem., Int. Ed. 44 (2005) 1665-1668
42. Hernández-Torres J.M., Achkar J., and Wei A. J. Org. Chem. 69 (2004) 7206-7211
43. Sherman A.A., Mironov Y.V., Yudina O.N., and Nifantiev N.E. Carbohydr. Res. 338 (2003) 697-703
44. Wang C.-C., Luo S.-Y., Shie C.-R., and Hung S.-C. Org. lett. 4 (2002) 847-849
45. Debenham A.D., and Toone E.J. Tetrahedron: Asymmetry 11 (2000) 385-387
46. Dandapani S., Jeske M., and Curran D.P. Proc. Natl. Acad. Sci. U.S.A 101 (2004) 12008-12012
47. Rocaboy C., Rutherford D., Bennett B.L., and Gladys J.A. J. Phys. Org. Chem. 13 (2000) 596-603
48. Abe T., Haga T., Negi S., Morita Y., Takayanagi K., and Hamamura K. Tetrahedron 57 (2001) 2701-2710
49. ® Silica gel 40 μm is available from Fluka.
50. When the products were dried under reduced pressure at 40-50 °C, the weights of 4a-c reached constant values but those of 11a-c continued to decrease gradually.
51. Schmidt R.R., and Michel J. Angew. Chem., Int. Ed. Engl. 19 (1980) 731-732
52. Schmidt R.R., and Michel J. Angew. Chem. Int. Ed. 61 (1986) 212-235
53. For short reviews, see:. Fugedi P., Garegg P.J., Loehn H., and Norberg T. J. Glycoconjugate 4 (1987) 97-108
54. Sinay P. Pure Appl. Chem. 63 (1991) 519-528
55. Schmidt R.R., and Stumpp M. Liebigs Ann. Chem. 7 (1983) 1249-1256
56. 13C NMR analysis; the methyl protons and the methyl carbon of the orthoester were observed at δ 1.64 ppm and 123.1 ppm, respectively.
57. Kong F. Carbohydr. Res. 342 (2007) 345-347
58. Wang W., and Kong F. Angew. Chem., Int. Ed. 38 (1999) 1247-1250
59. Wang W., and Kong F. J. Org. Chem. 63 (1998) 5744-5745
60. Rio S., Beau J.M., and Jacquinet J.C. Carbohydr. Res. 219 (1991) 71-90
61. Schmidt R.R., Michel J., and Roos M. Liebigs Ann. Chem. 7 (1984) 1343-1357
62. Phenyl 2,3,4,5-tetra-O-acetyl-1-thio-β-d-galactopyranoside 18 was purchased from TCI CO., LTD.
63. Fukunaga K., Yoshida M., Uematsu R., Hara M., Inoue S., Kondo H., and Nishimura S. Bioorg. Med. Chem. Lett. 13 (2003) 813-815
64. Schmidt R.R., Behrendt M., and Toepfer A. Synlett 11 (1990) 694-696
65. Vanker Y.D., Vanker P.S., Behrendt M., and Schmidt R.R. Tetrahedron 47 (1991) 9985-9992
66. Schmidt R.R., and Michel J. J. Carbohydr. Chem. 4 (1985) 141-169
67. Schmidt R.R., and Rücker E. Tetrahedron Lett. 21 (1980) 1421-1424