-
3
-
-
0027950416
-
-
Lemieux, R. U.; Du, M.-H.; Spohr, U. J. Am. Chem. Soc. 1994, 116, 9803-9804.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 9803-9804
-
-
Lemieux, R.U.1
Du, M.-H.2
Spohr, U.3
-
4
-
-
0004231915
-
-
CRC Press: Boca Raton
-
Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995; Levy, D.; Tang, C. The Synthesis of C-Glycosides; Elsevier/Pergamon: Oxford, 1995.
-
(1995)
C-Glycoside Synthesis
-
-
Postema, M.H.D.1
-
5
-
-
0010396923
-
-
Elsevier/Pergamon: Oxford
-
Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995; Levy, D.; Tang, C. The Synthesis of C-Glycosides; Elsevier/Pergamon: Oxford, 1995.
-
(1995)
The Synthesis of C-Glycosides
-
-
Levy, D.1
Tang, C.2
-
6
-
-
0032508934
-
-
Ravishankar, R.; Surolia, A.; Vijayan, M.; Lim, S.; Kishi, Y. J. Am. Chem. Soc. 1998, 120, 11297-11203.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 11297-111203
-
-
Ravishankar, R.1
Surolia, A.2
Vijayan, M.3
Lim, S.4
Kishi, Y.5
-
7
-
-
0344311770
-
-
Martin-Lomas, M.; Imberty, A.; Cañada, F. J.; Jimenez-Barbero, J. J. Am. Chem. Soc. 1998, 120, 1309-1318.
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 1309-1318
-
-
Martin-Lomas, M.1
Imberty, A.2
Cañada, F.J.3
Jimenez-Barbero, J.4
-
8
-
-
0026485171
-
-
Nagy, J. O.; Wang, P.; Gilbert, J. H.; Schaefer, M. E.; Hill, T. G.; Callstrom, M. R.; Bednarski, M. D. J. Med. Chem. 1992, 35, 4501-4502. Mortell, K. H.; Weatherman, R. V.; Kiessling, L. L. J. Am. Chem. Soc. 1996, 118, 2297-2298.
-
(1992)
J. Med. Chem.
, vol.35
, pp. 4501-4502
-
-
Nagy, J.O.1
Wang, P.2
Gilbert, J.H.3
Schaefer, M.E.4
Hill, T.G.5
Callstrom, M.R.6
Bednarski, M.D.7
-
9
-
-
0029870744
-
-
Nagy, J. O.; Wang, P.; Gilbert, J. H.; Schaefer, M. E.; Hill, T. G.; Callstrom, M. R.; Bednarski, M. D. J. Med. Chem. 1992, 35, 4501-4502. Mortell, K. H.; Weatherman, R. V.; Kiessling, L. L. J. Am. Chem. Soc. 1996, 118, 2297-2298.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 2297-2298
-
-
Mortell, K.H.1
Weatherman, R.V.2
Kiessling, L.L.3
-
10
-
-
15444347630
-
-
Hirschmann, R.; Hynes, J., Jr.; Cichy-Knight, M. A.; van Rijn, R. D.; Sprengeler, P. A.; Spoors, P. G.; Shakespeare, W. C.; Pientranico-Cole, S.; Barbosa, J.; Liu, J.; Yao, W.; Rohrer, S.; Smith, A. B., III. J. Med. Chem. 1998, 41, 1382-1391.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 1382-1391
-
-
Hirschmann, R.1
Hynes, J.J.2
Cichy-Knight, M.A.3
Van Rijn, R.D.4
Sprengeler, P.A.5
Spoors, P.G.6
Shakespeare, W.C.7
Pientranico-Cole, S.8
Barbosa, J.9
Liu, J.10
Yao, W.11
Rohrer, S.12
Smith A.B. III13
-
11
-
-
0032504013
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4817-4820
-
-
Ben, R.N.1
Orellana, A.2
Arya, P.3
-
12
-
-
0032546195
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1998)
Tetrahedron
, vol.54
, pp. 2827-2832
-
-
Dondoni, A.1
Marra, A.2
Massi, A.3
-
13
-
-
0032578741
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8179-8182
-
-
Griffin, F.K.1
Murphy, P.V.2
Paterson, D.E.3
Taylor, R.J.K.4
-
14
-
-
0032487986
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 8225-8228
-
-
Belica, P.S.1
Franck, R.W.2
-
15
-
-
0032568331
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 1709-1712
-
-
Evans, D.A.1
Trotter, B.W.2
Côté, B.3
-
16
-
-
0030795023
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 4204-4205
-
-
Spencer, R.P.1
Schwartz, J.2
-
17
-
-
0344273859
-
-
Recent examples of less complex C-glycosides, see: Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63, 4817-4820. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832. Griffin, F. K.; Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 8179-82. Belica, P. S.; Franck, R. W. Tetrahedron Lett. 1998, 39, 8225-8228. Evans, D. A.; Trotter, B. W.; Côté, B. Tetrahedron Lett. 1998, 39, 1709-1712. Spencer, R. P.; Schwartz, J. J. Org. Chem. 1997, 62, 4204-4205. Johnson, C. R.; Johns, B. A. Synth. Lett. 1998, 1406-1408.
-
(1998)
Synth. Lett.
, pp. 1406-1408
-
-
Johnson, C.R.1
Johns, B.A.2
-
18
-
-
0345136293
-
-
note
-
For "true" C-glycosides only the intersaccharide oxygen of the O-saccharide is replaced by a methylene. These should be distinguished from analogues which have longer or substituted intersaccharide linkers and modified aglycon segments, and are less synthetically challenging. In general, existing approaches to C-glycosides are more easily easily applied to the latter than the former.
-
-
-
-
20
-
-
84988075072
-
-
Glycal nucleophiles: Eisele, T.; Ishida, M.; Hummel, G.; Schmidt, R. Liebigs Ann. 1995, 2113-2121.
-
(1995)
Liebigs Ann.
, pp. 2113-2121
-
-
Eisele, T.1
Ishida, M.2
Hummel, G.3
Schmidt, R.4
-
21
-
-
0032575153
-
-
Cl radicals: Rubinstenn, G.; Mallet, J.-M.; Sinaÿ, P. Tetrahedon Lett. 1998, 39, 3697-3700.
-
(1998)
Tetrahedon Lett.
, vol.39
, pp. 3697-3700
-
-
Rubinstenn, G.1
Mallet, J.-M.2
Sinaÿ, P.3
-
22
-
-
0002015615
-
-
Cl electrophiles: Rouzad, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354. Preuss, R.; Schmidt, R. R. J. Carbohydr. Chem. 1991, 10, 887-900.
-
(1983)
J. Chem. Soc., Chem. Commun.
, pp. 1353-1354
-
-
Rouzad, D.1
Sinaÿ, P.2
-
23
-
-
0001664904
-
-
Cl electrophiles: Rouzad, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354. Preuss, R.; Schmidt, R. R. J. Carbohydr. Chem. 1991, 10, 887-900.
-
(1991)
J. Carbohydr. Chem.
, vol.10
, pp. 887-900
-
-
Preuss, R.1
Schmidt, R.R.2
-
24
-
-
0001247835
-
-
and refs 16 and 17
-
De novo approaches: Wang, Y.; Babirad, S. A.; Kishi, Y. J. Org. Chem. 1992, 57, 468-481 and refs 16 and 17.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 468-481
-
-
Wang, Y.1
Babirad, S.A.2
Kishi, Y.3
-
26
-
-
0021986893
-
-
Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256-1268. Jacques, F.; Dupeyroux, H.; Joly, J.-P.; Chapleur; Y. Tetrahedron Lett. 1997, 38, 73-76.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 1256-1268
-
-
Danishefsky, S.J.1
Pearson, W.H.2
Harvey, D.F.3
Maring, C.J.4
Springer, J.P.5
-
27
-
-
0031013014
-
-
Danishefsky, S. J.; Pearson, W. H.; Harvey, D. F.; Maring, C. J.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1256-1268. Jacques, F.; Dupeyroux, H.; Joly, J.-P.; Chapleur; Y. Tetrahedron Lett. 1997, 38, 73-76.
-
(1997)
Tetrahedron Lett.
, vol.38
, pp. 73-76
-
-
Jacques, F.1
Dupeyroux, H.2
Joly, J.-P.3
Chapleur, Y.4
-
28
-
-
0000356249
-
-
Shan, W.; Wilson, P.; Liang, W.; Mootoo, D. R. J. Org. Chem. 1994, 59, 7986-7992.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 7986-7992
-
-
Shan, W.1
Wilson, P.2
Liang, W.3
Mootoo, D.R.4
-
29
-
-
0004111991
-
-
D-Lyxose may be also obtained in one step, from calcium D-galactonate: Academic Press: London
-
D-Lyxose may be also obtained in one step, from calcium D-galactonate: Methods in Carbohydrate Chemistry; Whistler, R. L., Wolfrom, M. L., Eds.; Academic Press: London, 1962; Vol. 1, pp 77-78.
-
(1962)
Methods in Carbohydrate Chemistry
, vol.1
, pp. 77-78
-
-
Whistler, R.L.1
Wolfrom, M.L.2
-
31
-
-
33748244854
-
-
De Armas, P.; Francisco, C. G.; Suarez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774.
-
(1992)
Angew. Chem., Int. Ed. Engl.
, vol.31
, pp. 772-774
-
-
De Armas, P.1
Francisco, C.G.2
Suarez, E.3
-
32
-
-
0000460451
-
-
8b
-
For precursors to 8b-e, see: Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386 (8b); Wilson, P.; Jammalamadaka, V.; Mootoo, D. R. J. Carbohydr. Chem. 1994, 13, 841-849 (8c); ref 15, (8d); Reinhardt, G.; J. App. Biochem. 1980, 2, 495-509 (8e).
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 2383-2386
-
-
Hosomi, A.1
Sakata, Y.2
Sakurai, H.3
-
33
-
-
84959942307
-
-
8c; ref 15, (8d)
-
For precursors to 8b-e, see: Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386 (8b); Wilson, P.; Jammalamadaka, V.; Mootoo, D. R. J. Carbohydr. Chem. 1994, 13, 841-849 (8c); ref 15, (8d); Reinhardt, G.; J. App. Biochem. 1980, 2, 495-509 (8e).
-
(1994)
J. Carbohydr. Chem.
, vol.13
, pp. 841-849
-
-
Wilson, P.1
Jammalamadaka, V.2
Mootoo, D.R.3
-
34
-
-
0019253589
-
-
8e.
-
For precursors to 8b-e, see: Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386 (8b); Wilson, P.; Jammalamadaka, V.; Mootoo, D. R. J. Carbohydr. Chem. 1994, 13, 841-849 (8c); ref 15, (8d); Reinhardt, G.; J. App. Biochem. 1980, 2, 495-509 (8e).
-
(1980)
J. App. Biochem.
, vol.2
, pp. 495-509
-
-
Reinhardt, G.1
-
35
-
-
84985520823
-
-
Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522-523.
-
(1978)
Angew. Chem., Int. Ed. Engl.
, vol.17
, pp. 522-523
-
-
Neises, B.1
Steglich, W.2
-
36
-
-
0000987676
-
-
Pine, S. H.; Pettit, R. J.; Geib, G. D.; Cruz, S. G.; Gallego, C. H.; Tijerina, T.; Pine, R. D. J. Org. Chem. 1985, 50, 1212-1218.
-
(1985)
J. Org. Chem.
, vol.50
, pp. 1212-1218
-
-
Pine, S.H.1
Pettit, R.J.2
Geib, G.D.3
Cruz, S.G.4
Gallego, C.H.5
Tijerina, T.6
Pine, R.D.7
-
37
-
-
0031527779
-
-
See Supporting Information
-
Barili, P. L.; Catelani, G.; D'Andrea, F.; Mastrorilli, E. J. Carbohydr. Chem. 1997, 16, 1001-10. See Supporting Information.
-
(1997)
J. Carbohydr. Chem.
, vol.16
, pp. 1001-1010
-
-
Barili, P.L.1
Catelani, G.2
D'Andrea, F.3
Mastrorilli, E.4
-
38
-
-
0021999503
-
-
Feizi, T. Nature 1985, 314, 53-57.
-
(1985)
Nature
, vol.314
, pp. 53-57
-
-
Feizi, T.1
-
40
-
-
0021749125
-
-
Bremer, E. G.; Levery, S. B.; Sonnino, S. B.; Ghidoni, R.; Canevari, S.; Kannagi, R.; Hakomori, S. J. Biol. Chem. 1984, 259, 14773-14777.
-
(1984)
J. Biol. Chem.
, vol.259
, pp. 14773-14777
-
-
Bremer, E.G.1
Levery, S.B.2
Sonnino, S.B.3
Ghidoni, R.4
Canevari, S.5
Kannagi, R.6
Hakomori, S.7
-
41
-
-
0027749278
-
-
Boren, T.; Falk, P.; Rock, K. A.; Larson, G. Normack, S. Science 1993, 262, 1892-1895.
-
(1993)
Science
, vol.262
, pp. 1892-1895
-
-
Boren, T.1
Falk, P.2
Rock, K.A.3
Larson, G.4
Normack, S.5
-
43
-
-
0029770463
-
-
Marino-Albernas, J. R.; Bittman, R.; Peters, A.; Mayhew, E. J. Med. Chem. 1996, 39, 3241-3247.
-
(1996)
J. Med. Chem.
, vol.39
, pp. 3241-3247
-
-
Marino-Albernas, J.R.1
Bittman, R.2
Peters, A.3
Mayhew, E.4
-
44
-
-
0031504106
-
-
Tanahashi, E.; Murase, K.; Shibuga, M.; Igarashi, Y.; Ishida, H.; Hasegawa, A.; Kiso, M. J. Carbohydrate. Chem. 1997, 16, 831-858.
-
(1997)
J. Carbohydrate. Chem.
, vol.16
, pp. 831-858
-
-
Tanahashi, E.1
Murase, K.2
Shibuga, M.3
Igarashi, Y.4
Ishida, H.5
Hasegawa, A.6
Kiso, M.7
-
45
-
-
0029904740
-
-
Hiruma, K.; Kajimoto, T.; Weitz-Schmidt, G.; Ollmann, I., Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 9265-9270.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9265-9270
-
-
Hiruma, K.1
Kajimoto, T.2
Weitz-Schmidt, G.3
Ollmann, I.4
Wong, C.-H.5
-
46
-
-
0344273853
-
-
note
-
4,5 = 2.6 Hz.
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