Chemistry of 1-methylenesugars: synthetic utilizations to 1'-C-methyl-saccharides and related carbohydrates

Heterocycles

Volumn 78, Issue 1, 2009, Pages 19-44

  Namme, Rie ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

Glycosidation; 1,3 Dipolar Cycloaddition; 1 C Methyltrehalose; 1 Methylenesugar; spiro Ketodisaccharide

Indexed keywords

EID: 62549115717     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-08-638     Document Type: Review

References (55)

1. Takahashi H., Kittaka H., and Ikegami S. J. Synth. Org. Chem. Japan 58 (2000) 120
2. Sawada D., Takahashi H., Shiro M., and Ikegami S. Tetrahedron Lett. 46 (2005) 2399
3. Sawada D., Sasayama S., Takahashi H., and Ikegami S. Heterocycles 66 (2005) 441
4. Takahashi H., Shida T., Hitomi Y., Iwai Y., Miyama N., Nishiyama K., Sawada D., and Ikegami S. Chem. Eur. J. 12 (2006) 5861
5. Sawada D., Sasayama S., Takahashi H., and Ikegami S. Tetrahedron Lett. 47 (2006) 7219
6. Sawada D., Sasayama S., Takahashi H., and Ikegami S. Eur. J. Org. Chem. (2007) 1064
7. Sawada D., Sasayama S., Takahashi H., and Ikegami S. Tetrahedron 64 (2008) 8780
8. Ohtake H., Li X., Takahashi H., and Ikegami S. J. Synth. Org. Chem. Japan 60 (2002) 206
9. Taillefumier C., and Chapleur Y. Chem. Rev. 104 (2004) 263
10. Lay L., Nicotra F., Panza L., Russo G., and Caneva E. J. Org. Chem. 57 (1992) 1304
11. Griffin F.K., Murohy P.V., Paterson D.E., and Taylor R.J.K. Tetrahedron Lett. 39 (1998) 8179
12. Alcaraz M.-L., Griffin F.K., Paterson D.E., and Taylor R.J.K. Tetrahedron Lett. 39 (1998) 8183
13. Brockhaus M., and Lehmann J. Carbohydr. Res. 53 (1977) 21
14. Lehmann J., and Knapp C. Carbohydr. Res. 63 (1978) 257
15. Lancelin J.M., Pougny J.R., and Sinay P. Carbohydr. Res. 136 (1985) 369
16. Rajan Babu T.V., and Reddy G.S. J. Org. Chem. 51 (1986) 5458
17. Wilcox C.S., Long G.W., and Suh H. Tetrahedron Lett. 25 (1984) 395
18. Johson C.R., and Johons B.A. Synlett (1997) 1406
19. Csuk R., and Glänzer B.I. Tetrahedron 47 (1991) 1655
20. Li X., Ohtake H., Takahashi H., and Ikegami S. Tetrahedron 57 (2001) 4283
21. Hehre E.J., Brewer C.F., Uchiyama T., Schlesselmann P., and Lehmann J. Biochemistry 19 (1980) 357
22. Namme R., Mitsugi T., Takahashi H., Shiro M., and Ikegami S. Tetrahedron 62 (2006) 9183
23. For intramolecular glycosidation, see. Kobayashi T., Regens C.S., and Denmark S.E. J. Synth. Org. Chem. Japan 66 (2008) 616
24. Friesen R.W., and Sturino C.F. J. Org. Chem. 55 (1990) 5808
25. Dubois E., and Beau J.-M. Tetrahedron Lett. 31 (1990) 5165
26. In: Horton D. (Ed). Advances in Carbohydrate Chemistry and Biochemistry Vol. 51 (1995), Academic, San Diego 15-61
27. The glycosidation of 1-methylenesugar 2a with 2,4,6-tri-O-benzyl-D-glycono-1,5-lactone (11) with TsOH afforded α-disaccharide 21a and a small amount of β-disaccharide 21a(β). This was the only substrate that we could obtain β-isomer. Our attempt to anomerize α-glycoside into β-glycoside was unsuccessful. {A figure is presented}
28. Schlesselmann P., Fritz H., Lehmann J., Uchiyama T., Brewer C.F., and Hehre E.J. Biochemistry 21 (1982) 6606
29. Namme R., Mitsugi T., Takahashi H., and Ikegami S. Tetrahedron Lett. 46 (2005) 3033
30. Li X., Ohtake H., Takahashi H., and Ikegami S. Synlett (2001) 1885
31. Parish C.R., Freeman C., Brown K.J., Francis D.J., and Cowden W.B. Cancer Res. 59 (1999) 3433
32. For a review see:. Khachigian L.M., and Parish C.R. Drug Rev. 22 (2004) 1
33. Li X., Ohtake H., Takahashi H., and Ikegami S. Tetrahedron 57 (2001) 4297
34. Yamanoi T., Oda Y., Yamazaki I., Shinbara M., Morimoto K., and Matsuda S. Lett. Org. Chem. 2 (2005) 242
35. For example. In: Boons G.-J. (Ed). Carbohydrate Chemistry (1998), Blakie Academic & Professional, London 10-16
36. Namme R., Mitsugi T., Takahashi H., and Ikegami S. Eur. J. Org. Chem. (2007) 3758
37. Crowe L.M., and Crowe J.H. Biochim. Biophys. Acta 946 (1988) 193
38. Colaço C., Sen S., Thangarelu M., Pinder S., and Roser B. Biotechnology 10 (1992) 1007
39. Colaco C.A.L.S., Smith C.J.S., Sen S., Roser D.H., Newman Y., Ring S., and Roser B.J. In: Cleland J.L., and Langer R. (Eds). Formulations and Delivery of Proteins and Peptides. Symposium Series No. 567 (1994), American Chemical Society, Washington, DC 222-240
40. Tietze L.-F., Fischer R., and Guder H.-J. Tetrahedron Lett. 23 (1982) 4661
41. Nashed E.M., and Glaudemans C.P.J. J. Org. Chem. 54 (1989) 6116
42. Qiu D.X., Wang F.Y., and Cai M.S. Synth. Commun. 19 (1989) 3453
43. Kolar C., and Kneissl G. Angew. Chem. Int. Ed. Engl. 29 (1990) 809
44. Priebe W., Grynkiewicz G., and Neamati N. Tetrahedron Lett. 32 (1991) 2079
45. Mukaiyama T., and Matsubara K. Chem. Lett. (1992) 1041
46. Kirschning A., and Chen G.-W. Tetrahedron Lett. 40 (1999) 4665
47. Li X., Takahashi H., Ohtake H., and Ikegami S. Tetrahedron 57 (2001) 8053
48. Li X., Takahashi H., Ohtake H., and Ikegami S. Heterocycles 59 (2003) 547
49. Li X., Takahashi H., Ohtake H., and Ikegami S. Tetrahedron Lett. 45 (2004) 4123
50. Dondoni A., Franco S., Junquera F., Merino P., and Tejero T. Synth. Commun. 24 (1994) 2537
51. As only one example reported on the 1,3-dipolar cycloaddition, see. RajanBabu T.V., and Toma L. Carbohyd. Res. 51 (1986) 5458
52. Ohtake H., Ichiba N., Shiro M., and Ikegami S. J. Org. Chem. 65 (2000) 8164
53. Ohtake H., Ichiba N., and Ikegami S. J. Org. Chem. 65 (2000) 8171
54. Ohtake H., and Ikegami S. Org. Lett. 2 (2000) 457
55. Ohtake H., Li X., Shiro M., and Ikegami S. Tetrahedron 56 (2000) 7109