Synthesis of C-linked analogues of β-d-galactopyranosyl-(1→3)-d-galactopyranosides and of β-d-galactopyranosyl-(1→3)-d-galactal

Rademacher, 1988, Annu. Rev. Biochem., 57, 785, 10.1146/annurev.bi.57.070188.004033 Lis, 1993, Eur. J. Biochem., 218, 1, 10.1111/j.1432-1033.1993.tb18347.x Hart, 1992, Curr. Opin. Cell. Biol., 4, 1017, 10.1016/0955-0674(92)90134-X Varki, 1994, 71, 10.1007/978-1-4615-2401-4_3 Sears, 1999, Angew. Chem., Int. Ed., 38, 2301, 10.1002/(SICI)1521-3773(19990816)38:16<2300::AID-ANIE2300>3.0.CO;2-6 Bertozzi, 2001, Science (Washington, DC), 291, 2357, 10.1126/science.1059820 Rudd, 2001, Science (Washington, DC), 291, 2370, 10.1126/science.291.5512.2370 1997 Sears, 1996, Proc. Natl. Acad. Sci. U.S.A., 93, 12086, 10.1073/pnas.93.22.12086 Kiessling, 1996, Chem. Biol., 3, 71, 10.1016/S1074-5521(96)90280-X Beuth, 1995, Glycoconjugate J., 12, 1, 10.1007/BF00731862 Lasky, 1995, Annu. Rev. Biochem., 64, 113, 10.1146/annurev.bi.64.070195.000553 Toyokuni, 1995, Chem. Soc. Rev., 24, 231, 10.1039/cs9952400231 Varki, 1994, Proc. Natl. Acad. Sci. U.S.A., 91, 7390, 10.1073/pnas.91.16.7390 Feizi, 1993, Curr. Opin. Struct. Biol., 3, 701, 10.1016/0959-440X(93)90053-N Hakkomori, 1991, Curr. Opin. Immun., 3, 646, 10.1016/0952-7915(91)90091-E Wharton, 1989 Alper, 2001, Science (Washington, DC), 291, 2338, 10.1126/science.291.5512.2338 Bols, 1998, Acc. Chem. Res., 31, 1, 10.1021/ar970058r Barchi, 2000, Curr. Pharm. Des., 6, 485, 10.2174/1381612003400876 Musser, 1996, Pharm. News, 3, 11 Mulligan, 1993, Nature (London), 364, 149, 10.1038/364149a0 Ragupathi, 1999, Cancer Immunol. Immunother., 48, 1, 10.1007/s002620050542 MacLean, 1994, Can. J. Oncol., 4, 249 MacLean, 1993, Cancer Immunol. Immunother., 36, 215, 10.1007/BF01740902 Platt, 1997, Science (Washington, DC), 276, 428, 10.1126/science.276.5311.428 Levy, 1995 Postma, 1995 Du, 1998, Tetrahedron, 54, 9913, 10.1016/S0040-4020(98)00405-0 Springer, 1984, Science (Washington, DC), 224, 1198, 10.1126/science.6729450 Jennings, 1987, Can. Prog. Biotechnol., 3, 149 Taylor-Papadimitriou, 1994, Trends Biotechnol., 12, 227, 10.1016/0167-7799(94)90121-X MacLean, 1994, Cancer Invest., 12, 46, 10.3109/07357909409021392 Rye, 1995, Glycobiology, 5, 385, 10.1093/glycob/5.4.385 Springer, 1995, Crit. Rev. Oncol., 6, 57, 10.1615/CritRevOncog.v6.i1.50 Ragupathi, 1996, Cancer Immunol. Immunother., 43, 152, 10.1007/s002620050316 Cooper, 1997, Glycobiology in Xenontransplantation research, 531 Kim, 1997, Glycoconjugate J., 14, 569, 10.1023/A:1018580324971 Hakomori, 1997, Chem. Biol., 4, 97, 10.1016/S1074-5521(97)90253-2 Hallberg, 1998, Xenotransplantation, 5, 246, 10.1111/j.1399-3089.1998.tb00035.x Hakomori, 1998, Acta Anat., 161, 79, 10.1159/000046451 Kuduk, 1998, J. Am. Chem. Soc., 120, 12474, 10.1021/ja9825128 Orntoft, 1999, Electrophoresis, 20, 362, 10.1002/(SICI)1522-2683(19990201)20:2<362::AID-ELPS362>3.0.CO;2-V Lo-Man, 1999, Cancer Res., 59, 1520 Allen, 1999, J. Am. Chem. Soc., 121, 10875, 10.1021/ja992594f Kuberan, 2000, Curr. Org. Chem., 4, 653, 10.2174/1385272003376111 Bousquet, 2000, J. Carbohydr. Chem., 19, 527, 10.1080/07328300008544097 Pasquarello, 1999, Bioorg. Med. Chem. Lett., 9, 793, 10.1016/S0960-894X(99)00064-5 Pasquarello, 2000, J. Org. Chem., 65, 4251, 10.1021/jo991952u Rodén, 1970, Vol. 2, 245 Stern, 1971, J. Biol. Chem., 246, 5707, 10.1016/S0021-9258(18)61863-0 Montreuil, 1980, Adv. Carbohydr. Chem. Biochem., 37, 157, 10.1016/S0065-2318(08)60021-9 Hirst, 1954, J. Chem. Soc., 2622, 10.1039/jr9540002622 Bailey, 1965 Aspinall, 1965, J. Chem. Soc., 3003, 10.1039/jr9650003003 Hirst, 1965, J. Chem. Soc., 2958, 10.1039/jr9650002958 Parikh, 1966, Can. J. Chem., 44, 1531, 10.1139/v66-228 Rodén, 1966, J. Biol. Chem., 241, 5949, 10.1016/S0021-9258(18)96362-3 Lindberg, 1966, Carbohydr. Res., 2, 413, 10.1016/S0008-6215(00)80336-5 Michalski, 1984, Clin. Chim. Acta, 137, 43, 10.1016/0009-8981(84)90310-3 Fritzsimmons, 1988, J. Am. Chem. Soc., 110, 5229, 10.1021/ja00223a073 Halcomb, 1989, J. Am. Chem. Soc., 111, 6661, 10.1021/ja00199a028 Sebesta, 1992, J. Org. Chem., 57, 4799, 10.1021/jo00044a010 Liu, 1993, Science, 260, 1307, 10.1126/science.8493573 Wang, 1993, Tetrahedron Lett., 34, 4881, 10.1016/S0040-4039(00)74036-6 Liu, 1994, J. Org. Chem., 59, 1892, 10.1021/jo00086a047 Randolph, 1995, J. Am. Chem. Soc., 117, 5693, 10.1021/ja00126a010 Danishefsky, 1995, J. Am. Chem. Soc., 117, 5701, 10.1021/ja00126a011 Kim, 2004, J. Am. Chem. Soc., 126, 1336, 10.1021/ja039746y Geiger, 2004, Synthesis, 836 Marouka, 1987, Chem. Lett., 2215, 10.1246/cl.1987.2215 Casiraghi, 1989, Carbohydr. Res., 191, 243, 10.1016/0008-6215(89)85068-2 Daves, 1990, Acc. Chem. Res., 23, 201, 10.1021/ar00174a006 Dubois, 1992, Carbohydr. Res., 228, 103, 10.1016/S0008-6215(00)90552-4 Toshima, 1994, Tetrahedron Lett., 35, 5673, 10.1016/S0040-4039(00)77276-5 Lopez, 1995, J. Org. Chem., 60, 3871, 10.1021/jo00117a044 Thorn, 1996, Synlett, 185, 10.1055/s-1996-5346 Williams, 2000, Carbohydr. Chem. Biol., 1, 61, 10.1002/9783527618255.ch3 Berber, 2001, Chemistry (Weinheim), 7, 903 Ramnauth, 2001, Org. Lett., 3, 2013, 10.1021/ol010070q Yadav, 2001, Carbohydr. Res., 221, 10.1016/S0008-6215(01)00087-8 Hayashi, 2001, Recent Res. Develop. Org. Bioorg. Chem., 4, 63 Parrish, 2002, Org. Lett., 4, 1439, 10.1021/ol025575a Hayashi, 2003, Chirality, 15, 10, 10.1002/chir.10146 Seeberger, 2003, Chem. Commun., 1115, 10.1039/b210230g Geiger, 2004, Synlett, 836 Kim, 2004, J. Am. Chem. Soc., 126, 1336, 10.1021/ja039746y Miller, 1988, J. Org. Chem., 53, 5580, 10.1021/jo00258a046 Wang, 1988, J. Org. Chem., 53, 4151, 10.1021/jo00252a065 Paton, 1998, 49 Vogel, 1998, 19 Krintel, 1999, Tetrahedron Lett., 40, 7565, 10.1016/S0040-4039(99)01604-4 Gerber, 1999, Tetrahedron Lett., 40, 3165, 10.1016/S0040-4039(99)00432-3 Skrydstrup, 2000, Vol. 1, 495 Liu, 2001, J. Am. Chem. Soc., 123, 8602, 10.1021/ja010641+ Liu, 2001, Curr. Org. Chem., 5, 1133, 10.2174/1385272013374699 Vauzeilles, 2001, Tetrahedron Lett., 42, 7269, 10.1016/S0040-4039(01)01533-7 Munch-Mikkelsen, 2002, J. Org. Chem., 67, 6297, 10.1021/jo020339z Postema, 2003, J. Org. Chem., 68, 4748, 10.1021/jo030039x Stepànek, 2003, Synlett, 963 Cardona, 2003, Org. Lett., 5, 1475, 10.1021/ol0342507 Stephànek, 2004, Tetrahedron: Asymmetry, 15, 1033, 10.1016/j.tetasy.2004.01.023 Dondoni, 2004, Chem. Rev., 104, 2557, 10.1021/cr020079l Schmidt, 1992, Liebigs Ann. Chem., 983, 10.1002/jlac.1992199201161 Itoh, 1980, Tetrahedron Lett., 21, 361, 10.1016/S0040-4039(01)85473-3 Itoh, 1981, Bull. Chem. Soc. Jpn., 54, 274, 10.1246/bcsj.54.274 Horton, 1996, J. Org. Chem., 61, 3783, 10.1021/jo960032y Witczak, 1994 Zhu, 2000, Tetrahedron: Asymmetry, 11, 263, 10.1016/S0957-4166(99)00492-9 Jiménez-Barbero, 2001, J. Org. Chem., 66, 5132, 10.1021/jo0102462 Kobertz, 1992, Tetrahedron Lett., 737, 10.1016/S0040-4039(00)77703-3 Kobertz, 1996, J. Org. Chem., 61, 1894, 10.1021/jo9517095 Dondoni, 1996, Tetrahedron Lett., 37, 7587, 10.1016/0040-4039(96)01667-X Dondoni, 1994, J. Org. Chem., 59, 6404, 10.1021/jo00100a050 Dondoni, 1998, Synthesis, 1681, 10.1055/s-1998-2208 Dondoni, 2000, Synthesis, 22, 1701 Dondoni, 2000, Pure Appl. Chem., 72, 1577, 10.1351/pac200072091577 Zimmerman, 1957, J. Am. Chem. Soc., 79, 1920, 10.1021/ja01565a041 Rychnovsky, 1998, Acc. Chem. Res., 31, 9, 10.1021/ar960223n Lemieux, 1964, Can. J. Chem., 42, 1417 Lemieux, 1965, Can. J. Chem., 43, 1468 Thiem, 1978, Synthesis, 696, 10.1055/s-1978-24863 Thiem, 1984, J. Carbohydr. Chem., 3, 287, 10.1080/07328308408058822 Friesen, 1990, Tetrahedron, 46, 103, 10.1016/S0040-4020(01)97587-8 Kottenhahn, 1991, Liebigs Ann. Chem., 22, 727, 10.1002/jlac.1991199101127 Tatsuta, 1977, Carbohydr. Res., 54, 85, 10.1016/S0008-6215(00)80558-3 Friesen, 1989, J. Am. Chem. Soc., 111, 6656, 10.1021/ja00199a027 Moreno-Vargas, 2003, Tetrahedron: Asymmetry, 14, 3173, 10.1016/j.tetasy.2003.08.021