DTBS effect: The unique sterically driven director for α-galactosylation

Heterocycles

Volumn 76, Issue 2, 2008, Pages 883-908

  Imamura, Akihiro ^a,b   Ando, Hiromune ^a,b   Ishida, Hideharu ^a   Kiso, Makoto ^a,b  

^a GIFU UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Carbohydrate; Di tert butylsilylene; Galactosylation; Protective Group; Stereoselectivity

Indexed keywords

EID: 61349115629     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-08-SR(N)4     Document Type: Article

References (82)

1. In: Varki A., Cummings R., Esko J., Freeze H., Hart G., and Marth J. (Eds). Essentials of Glycobiology (1999), Cold Spring Harbor Laboratory Press, New York
2. Toshima K., and Tatsuta K. Chem. Rev. 93 (1993) 1503
3. Jung K.-H., Müller M., and Schmidt R.R. Chem. Rev. 100 (2000) 4423
4. In: Kamerling J.P., Boons G.-J., Lee Y.C., Suzuki A., Taniguchi N., and Voragen A.G.J. (Eds). Comprehensive Glycoscience Vol. 1 (2007), Elsevier, Oxford
5. Goodman L. Adv. Carbohydr. Chem. Biochem. 22 (1967) 109
6. Hashimoto S., Hayashi M., and Noyori R. Tetrahedron Lett. 25 (1985) 1379
7. Lemieux R.U. Pure Appl. Chem. 25 (1971) 527
8. Ando H., Ishida H., and Kiso M. In: Osborn H.M.I. (Ed). Best Synthetic Methods: Carbohydrates (2003), Elsevier, Oxford 277-310
9. Halcomb R.L., and Chappell M.D. J. Carbohydr. Chem. 21 (2002) 723
10. Ito Y., and Ogawa T. Angew. Chem. Int. Ed. Engl. 33 (1994) 1765
11. Ito Y., Ando H., Wada M., Kawai T., Ohnishi Y., and Nakahara Y. Tetrahedron 57 (2001) 4123
12. Crich D., and Sun S. J. Org. Chem. 62 (1997) 1198
13. Crich D., and Chandrasekera N.S. Angew. Chem. Int. Ed. Engl. 43 (2004) 5386
14. Bongat A.F.G., and Demchenko A.V. Carbohydr. Res. (2007) 342 374 and references therein
15. Lemieux R.U., Hendriks K.B., Stick R.V., and James K. J. Am. Chem. Soc. 97 (1975) 4056
16. Demchenko A.V. Synlett 9 (2003) 1225
17. Koenigs W., and Knorr E. Chem. Ber. 34 (1901) 957
18. Wulff G., and Rohle G. Angew. Chem. Int. Ed. Engl. 13 (1974) 157
19. Demchenko A.V., Rousson E., and Boons G.-J. Tetrahedron Lett. 40 (1999) 6523
20. Schmidt R.R., and Jung K.H. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Marcel Dekker, Inc., New York 282
21. Paulsen H., and Stenzel W. Chem. Ber. (1978) 111 2334; idem. ibid., 1978, 111, 2348
22. Lemieux R.U., and Ratcliffe R.M. Can. J. Chem. 57 (1979) 1244
23. Winterfeld G.A., Ito Y., Ogawa T., and Schmidt R.R. Eur. J. Org. Chem. (1999) 1167
24. Geiger J., Reddy G., Winterfeld G.A., Weber R., Przybylski M., and Schmidt R.R. J. Org. Chem. 72 (2007) 4367
25. Kim J.-H., Yang H., Khot V., Whitfield D., and Boons G.-J. Eur. J. Org. Chem. (2006) 5007
26. Benakli K., Zha C., and Kerns R.J. J. Am. Chem. Soc. 123 (2001) 9461
27. Manabe S., Ishii K., and Ito Y. J. Am. Chem. Soc. 128 (2006) 10666
28. Demchenko A., Stauch T., and Boons G.-J. Synlett (1997) 818
29. Tokimoto H., Fujimoto Y., Fukase K., and Kusumoto S. Tetrahedron: Asymmetry 16 (2005) 441
30. Ishiwata A., Munemura Y., and Ito Y. Tetrahedron 64 (2008) 92
31. Ishiwata A., and Ito Y. Tetrahedron Lett. 46 (2005) 3521
32. Pedersen C.M., Nordstrθm L.U., and Bols M. J. Am. Chem. Soc. 129 (2007) 9222
33. Imamura A., Ando H., Korogi S., Tanabe G., Muraoka O., Ishida H., and Kiso M. Tetrahedron Lett. 44 (2003) 6725
34. Ratcliffe A.J., and Fraser-Reid B. J. Chem. Soc., Perkin Trans. 1 (1990) 747
35. Veeneman G.H., van Leeuwen S.H., and van Boom J.H. Tetrahedron Lett. 31 (1990) 1331
36. Konradsson P., Udodong U.E., and Fraser-Reid B. Tetrahedron Lett. 31 (1990) 4313
37. Dasgupta F., and Garegg P.J. Carbohydr. Res. 202 (1990) 225
38. Mukaiyama T., Murai Y., and Shoda S. Chem. Lett. (1981) 431
39. Suzuki K., Maeta H., Suzuki T., and Matsumoto T. Tetrahedron Lett. 30 (1989) 6879
40. Schmidt R.R. Angew. Chem. Int. Ed. Engl. 25 (1986) 212
41. van Boeckel C.A.A., Beetz T., and van Aelst S.F. Tetrahedron 40 (1984) 4097
42. Yamaguchi M., Horiguchi A., Fukuda A., and Minami T. J. Chem. Soc., Perkin Trans. 1 (1990) 1079
43. Brockhausen I. Biochem. Biophys. Acta 1473 (1999) 67
44. Brocke C., and Kunz H. Bioorg. Med. Chem. 10 (2002) 3085
45. Marcaurelle L.A., and Bertozzi C.R. Glycobiology 12 (2002) 69R
46. Furusawa K. Chem. Lett. (1989) 509
47. Ando H., Koike Y., Ishida H., and Kiso M. Tetrahedron Lett. 44 (2003) 6883
48. First report on the synthesis of glycophorin A. Nakahara Y., Iijima H., and Ogawa T. Tetrahedron Lett. 35 (1994) 3321
49. Schwarz J.B., Kuduk S.D., Chen X.-T., Sames D., Glunz P.W., and Danishefsky S.J. J. Am. Chem. Soc. 121 (1999) 2662
50. Imamura A., Kimura A., Ando H., Ishida H., and Kiso M. Chem. Eur. J. 12 (2006) 8862
51. Kimura A., Imamura A., Ando H., Ishida H., and Kiso M. Synlett 15 (2006) 2379
52. Natori N., Koezuka Y., and Higa T. Tetrahedron Lett. 34 (1993) 5591
53. Kinjo Y., Wu D., Kim G., Xing G.-W., Poles M.A., Ho D.D., Tsuji M., Kawahara K., Wong C.-H., and Kronenberg M. Nature 434 (2005) 520
54. Kawano T., Cui J., Koezuka Y., Toura I., Kaneko Y., Motoki K., Ueno H., Nakagawa R., Sato H., Kondo E., Koseki H., and Taniguchi M. Science 278 (1997) 1626
55. Zhou D., Mattner J., Cantu C., Schrantz N., Yin N., Gao Y., Sagiv Y., Hudspeth K., Wu Y.-P., Yamashita T., Teneberg S., Wang D., Proia R.L., Levery S.B., Savage P.B., Teyton L., and Bendelac A. Science 306 (2004) 1786
56. Takikawa H., Muto S.-E., and Mori K. Tetrahedron 54 (1998) 3141
57. Figueroa-Pérez S., and Schmidt R.R. Carbohydr. Res. 328 (2000) 95
58. Du W., and Gervay-Hague J. Org. Lett. 7 (2005) 2063
59. Xia C., Yao Q., Schümann J., Rossy E., Chen W., Zhu L., Zhang W., Libero G.D., and Wang P.G. Bioorg. Med. Chem. Lett. 16 (2006) 2195
60. Fan G.-T., Pan Y.-S., Lu K.-C., Cheng Y.-P., Lin W.-C., Lin S., Lin C.-H., Wong C.-H., Fang J.-M., and Lin C.-C. Tetrahedron 61 (2005) 1855
61. Ndonye R.M., Izmirian D.P., Dunn M.F., Yu K.O.A., Porcelli S.A., Khurana A., Kronenberg M., Richardson S.K., and Howell A.R. J. Org. Chem. 70 (2005) 10260
62. Koike K., Sugimoto M., Sato S., Ito Y., Nakahara Y., and Ogawa T. Carbohydr. Res. 163 (1987) 189
63. Yao Q., Song J., Xia C., Zhang W., and Wang P.G. Org. Lett. 8 (2006) 911
64. Kiso M., Nakamura A., Tomita Y., and Hasegawa A. Carbohydr. Res. 158 (1986) 101
65. Kiso M., Nakamura A., Nakamura J., Tomita Y., and Hasegawa A. J. Carbohydr. Chem. 5 (1986) 335
66. Borbás A., Csávás M., Szilágyi L., Májer G., and Lipták A. J. Carbohydr. Chem. 23 (2004) 133
67. Lee A., Farrand K.J., Dickgreber N., Hayman C.M., Mrs S., Hermans I.F., and Painter G.F. Carbohydr. Res. 341 (2006) 2785
68. Beutler E., and Kuhl W. J. Biol. Chem. 247 (1972) 7195
69. Casciola-Rosen L.A.F., and Hubbard A.L. J. Biol. Chem. 266 (1991) 4341
70. Courtin-Duchateau M.-C., and Veyrieres A. Carbohydr. Res. 65 (1978) 23
71. Szweda R., Spohr U., Lemieux R.U., Schindler D., Bishop D.F., and Desnick R.J. Can. J. Chem. 67 (1989) 1388
72. Imamura A., Ando H., Ishida H., and Kiso M. Org. Lett. 7 (2005) 4415
73. Yan F., Mehta S., Eichler E., Wakarchuk W.W., Gilbert M., Schur M.J., and Whitfield D.M. J. Org. Chem. 68 (2003) 2426
74. Mitsunobu O. Synthesis 1 (1981)
75. Tsunoda T., Yamamiya Y., and Ito S. Tetrahedron Lett. 34 (1993) 1639
76. Tsunoda T., Otsuka J., Yamamiya Y., and Ito S. Chem. Lett. (1994) 539
77. Tsunoda T., Yamamiya Y., Kawamura Y., and Ito S. Tetrahedron Lett. 36 (1995) 2529
78. O'Neil I.A., Thompson S., Murray C.L., and Kalindjian S.B. Tetrahedron Lett. 39 (1998) 7787
79. Miljković M., Yeagley D., Deslongchamps P., and Dory Y.L. J. Org. Chem. 62 (1997) 7597
80. Shuto S., Ishikawa S., Abe H., and Matsuda A. J. Synth. Org. Chem. Jpn. 66 (2008) 52
81. Tamura S., Abe H., Matsuda A., and Shuto S. Angew. Chem. Int. Ed. 42 (2003) 1021
82. Hada N., Oka J., Nishiyama A., and Takeda T. Tetrahedron Lett. 47 (2006) 6647