Design and use of an oxazolidine silyl enol ether as a new homoalanine carbanion equivalent for the synthesis of carbon-linked isosteres of O- glycosyl serine and N-glycosyl asparagine

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 933-944

  Dondoni, Alessandro ^a   Marra, Alberto ^a   Massi, Alessandro ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ASPARAGINE DERIVATIVE; ETHER DERIVATIVE; SERINE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CARBOHYDRATE ANALYSIS; CELL ADHESION; CELL MEMBRANE; GLYCOSYLATION; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0033525184     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981861h     Document Type: Article

References (65)

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8. Reviews: (a) Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294-308. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823- 839. (c) Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232. (d) Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63. (e) Arsequell, G.; Valencia, G. Tetrahedron Asymm. 1997, 8, 2839-2876. (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. For selected recent papers, see: Polt, R.; Szabó, Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104. Merritt, J. R.; Naisang, E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4443-4449. Dan, A.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1994, 36, 7487-7490. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353. Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem. Eur. J. 1997, 3, 1617- 1628.
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11. Reviews: (a) Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294-308. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823- 839. (c) Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232. (d) Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63. (e) Arsequell, G.; Valencia, G. Tetrahedron Asymm. 1997, 8, 2839-2876. (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. For selected recent papers, see: Polt, R.; Szabó, Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104. Merritt, J. R.; Naisang, E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4443-4449. Dan, A.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1994, 36, 7487-7490. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353. Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem. Eur. J. 1997, 3, 1617- 1628.
12. Reviews: (a) Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294-308. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823- 839. (c) Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232. (d) Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63. (e) Arsequell, G.; Valencia, G. Tetrahedron Asymm. 1997, 8, 2839-2876. (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. For selected recent papers, see: Polt, R.; Szabó, Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104. Merritt, J. R.; Naisang, E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4443-4449. Dan, A.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1994, 36, 7487-7490. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353. Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem. Eur. J. 1997, 3, 1617- 1628.
13. Reviews: (a) Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294-308. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823- 839. (c) Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232. (d) Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63. (e) Arsequell, G.; Valencia, G. Tetrahedron Asymm. 1997, 8, 2839-2876. (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. For selected recent papers, see: Polt, R.; Szabó, Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104. Merritt, J. R.; Naisang, E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4443-4449. Dan, A.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1994, 36, 7487-7490. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353. Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem. Eur. J. 1997, 3, 1617- 1628.
14. Reviews: (a) Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294-308. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823- 839. (c) Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232. (d) Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63. (e) Arsequell, G.; Valencia, G. Tetrahedron Asymm. 1997, 8, 2839-2876. (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. For selected recent papers, see: Polt, R.; Szabó, Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104. Merritt, J. R.; Naisang, E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4443-4449. Dan, A.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1994, 36, 7487-7490. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353. Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem. Eur. J. 1997, 3, 1617- 1628.
15. Reviews: (a) Kunz, H. Angew. Chem., Int. Ed. Engl. 1987, 26, 294-308. (b) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823- 839. (c) Kunz, H. Pure Appl. Chem. 1993, 65, 1223-1232. (d) Meldal, M.; Bock, K. Glycoconjugate J. 1994, 11, 59-63. (e) Arsequell, G.; Valencia, G. Tetrahedron Asymm. 1997, 8, 2839-2876. (f) Taylor, C. M. Tetrahedron 1998, 54, 11317-11362. For selected recent papers, see: Polt, R.; Szabó, Treiberg, J.; Li, Y.; Hruby, V. J. J. Am. Chem. Soc. 1992, 114, 10249-10258. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1994, 33, 1102-1104. Merritt, J. R.; Naisang, E.; Fraser-Reid, B. J. Org. Chem. 1994, 59, 4443-4449. Dan, A.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1994, 36, 7487-7490. Unverzagt, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2350-2353. Danishefsky, S. J.; Hu, S.; Cirillo, P. F.; Eckhardt, M.; Seeberger, P. H. Chem. Eur. J. 1997, 3, 1617-1628.
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19. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
20. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales-Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639-10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
21. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
22. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
23. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
24. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
25. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
26. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
27. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
28. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
29. For the synthesis of compounds in which isosteric replacement of the glycosidic oxygen or nitrogen with a methylene group has been carried out, see: (a) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197-200. (b) Bertozzi, C. R.; Cook, D. G.; Kobertz, W. R.; Gonzales- Scarano, F.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 10639- 10641. (c) Bertozzi, C. R.; Hoeprich, P. D., Jr.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092-6094. (d) Dorgan, B. J.; Jackson, R. F. W. Synlett 1996, 859-861. (e) Herpin, T. F.; Motherwell, W. B.; Weibel, J.-M. Chem. Commun. 1997, 923-924. (f) Burkhart, F.; Hoffmann, M.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1191-1192. (g) Lay, L.; Meldal, M.; Nicotra, F.; Panza, L.; Russo, G. Chem. Commun. 1997, 1469-1470. (h) Debenham, S. D.; Debenham, J. S.; Burk, M. J.; Toone, E. J. J. Am. Chem. Soc. 1997, 119, 9897-9898. (i) Urban, D.; Skrydstrup, T.; Beau, J.-M. Chem. Commun. 1998, 955-956. (j) Ben, R. N.; Orellana, A.; Arya, P. J. Org. Chem. 1998, 63 (3), 4817-4820. (k) Fuchss, T.; Schmidt, R. R. Synthesis 1998, 753-758.
30. Dondoni, A.; Marra, A.; Massi, A. Chem. Commun. 1998, 1741-1742.
31. Dondoni, A.; Massi, A.; Marra, A. Tetrahedron Lett. 1998, 39, 6601-6604.
32. (a) Levy, D. E.; Thang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995.
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37. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827-2832.
38. 2O, DMF, 0 °C to room temperature, 20 h) gave the corresponding 3-O-benzyl ether in only 20% yield. The main product was the α,β-unsaturated N-Boc amino ester (45%).
39. Rossi, L.; Pecunioso, A. Tetrahedron Lett. 1994, 35, 5285-5288.
40. Schmidt, R. R.; Michel, J.; Roos, M. Liebigs Ann. 1984, 1343-1357.
41. 6 at 120-140 °C; see Experimental Section).
42. Only traces of 8 were present in the crude reaction mixture. A partial desilylation of 1a to give 8 occurred during the chromatographic separation. Both compounds 8 and 1a were reused in appropriate reactions of Schemes 1 and 2, respectively.
43. 2, -20 °C.
44. (a) Ohrui, H.; Jones, G. H.; Moffatt, J. G.; Maddox, M. L.; Christensen, A. T.; Byram, S. K. J. Am. Chem. Soc. 1975, 97, 4602-4613.
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49. 4 oxidation of the alcohol), see ref 9c.
50. Only compound 26 had been originally reported by Bednarsky and co-workers (ref 5b). However, we have recently carried out an alternative synthesis of 26 and an adequate characterization (ref 10).
51. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 6; 818-826. Mukaiyama, T. Org. React. 1982, 28, 203-331.
52. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 6; 818- 826. Mukaiyama, T. Org. React. 1982, 28, 203-331.
53. Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404-6412.
54. This undesired reaction has been recently reported to occur also for 1,2-diol derivatives; see: Jung, P. M. J.; Burger, A.; Biellmann, J.-F. J. Org. Chem. 1997, 62, 8309-8314.
55. 2 either commercially available or prepared in situ.
56. 2 either commercially available or prepared in situ.
57. Dewey, R. S.; van Tamelen, E. E. J. Am. Chem. Soc. 1961, 83, 3729. Hart, D. J.; Hong, W.-P.; Hsu, L.-Y. J. Org. Chem. 1987, 52, 4665-4673.
58. Dewey, R. S.; van Tamelen, E. E. J. Am. Chem. Soc. 1961, 83, 3729. Hart, D. J.; Hong, W.-P.; Hsu, L.-Y. J. Org. Chem. 1987, 52, 4665-4673.
59. 2O was sluggish and gave variable amounts of byproducts such as α,β-unsaturated formyl C-glycosides (up to 40% in the manno series).
60. Wittman, V.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1091-1193.
61. The syntheses of one C-glycopeptide (ref 5c) and several O-glycopeptides (Fields, G. B.; Noble, R. L. Int. J. Peptide Protein Res. 1990, 35, 161-214) by the use of O-benzylated glycosyl amino acids have been reported.
62. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
63. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
64. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181-186.
65. Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277.