Ring opening of sialyllactones with glycine esters: Synthesis of selectively protected glycinyl-NeuAc saccharopeptides

Tetrahedron

Volumn 53, Issue 32, 1997, Pages 11039-11048

  Gervay, Jacquelyn ^a   Ramamoorthy, P S ^a   Mamuya, Nellie N ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; GLYCINE DERIVATIVE; N ACETYLNEURAMINIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030852173     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00364-5     Document Type: Article

References (37)

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2. For leading references see: Walz, G.; Aruffo, A.; Kolanus, W.; Polley, M.J.; Phillips, M.L. Wayner, E.; Nudelman, E.; Singhal, A.K.; Hakomori, S.; Paulson, J.C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224. Phillips, M.L., Nudelman, E.; Gaeta, F.C.A.; Perez, M.; Singhal, A.K.; Hakomori, S.-I.; Paulson, J.C. Science 1990, 250, 1130. Finne, J. TIBS, 1985, 129. Hakomori, S.-I. Cancer Res. 1985, 45, 2405. Fukushima, K.; Hirota, M.; Terasaki, P.I.; Wakisaka, A.; Togashi, H.; Chia, D.; Suyama, N.; Fukushi, Y.; Nudelman, E.; Hakomori, S.-I. Cancer Res. 1984, 44, 5279.
3. For leading references see: Walz, G.; Aruffo, A.; Kolanus, W.; Polley, M.J.; Phillips, M.L. Wayner, E.; Nudelman, E.; Singhal, A.K.; Hakomori, S.; Paulson, J.C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224. Phillips, M.L., Nudelman, E.; Gaeta, F.C.A.; Perez, M.; Singhal, A.K.; Hakomori, S.-I.; Paulson, J.C. Science 1990, 250, 1130. Finne, J. TIBS, 1985, 129. Hakomori, S.-I. Cancer Res. 1985, 45, 2405. Fukushima, K.; Hirota, M.; Terasaki, P.I.; Wakisaka, A.; Togashi, H.; Chia, D.; Suyama, N.; Fukushi, Y.; Nudelman, E.; Hakomori, S.-I. Cancer Res. 1984, 44, 5279.
4. For leading references see: Walz, G.; Aruffo, A.; Kolanus, W.; Polley, M.J.; Phillips, M.L. Wayner, E.; Nudelman, E.; Singhal, A.K.; Hakomori, S.; Paulson, J.C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224. Phillips, M.L., Nudelman, E.; Gaeta, F.C.A.; Perez, M.; Singhal, A.K.; Hakomori, S.-I.; Paulson, J.C. Science 1990, 250, 1130. Finne, J. TIBS, 1985, 129. Hakomori, S.-I. Cancer Res. 1985, 45, 2405. Fukushima, K.; Hirota, M.; Terasaki, P.I.; Wakisaka, A.; Togashi, H.; Chia, D.; Suyama, N.; Fukushi, Y.; Nudelman, E.; Hakomori, S.-I. Cancer Res. 1984, 44, 5279.
5. For leading references see: Walz, G.; Aruffo, A.; Kolanus, W.; Polley, M.J.; Phillips, M.L. Wayner, E.; Nudelman, E.; Singhal, A.K.; Hakomori, S.; Paulson, J.C. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 6224. Phillips, M.L., Nudelman, E.; Gaeta, F.C.A.; Perez, M.; Singhal, A.K.; Hakomori, S.-I.; Paulson, J.C. Science 1990, 250, 1130. Finne, J. TIBS, 1985, 129. Hakomori, S.-I. Cancer Res. 1985, 45, 2405. Fukushima, K.; Hirota, M.; Terasaki, P.I.; Wakisaka, A.; Togashi, H.; Chia, D.; Suyama, N.; Fukushi, Y.; Nudelman, E.; Hakomori, S.-I. Cancer Res. 1984, 44, 5279.
6. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
7. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
8. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
9. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
10. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
11. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
12. For lead references see: Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.O.; Bock, K. J. Am. Chem. Soc. 1995, 116, 1616. Sabesan, S.; Neira, S.; Wasserman, Z. Carbohydr. Res. 1995, 267, 239. Bandgar, B.P.; Patil, S.V.; Zbiral, E. Carbohydr. Res. 1995, 276, 337. von Itzstein, M.; Wu, W.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryn, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M. and Penn, C. R. J. Med. Chem. 1994, 37, 616-624. Drigues, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297. Unverzagt, C. Angew. Chem. Int. Ed. Engl. 1993, 32, 1691. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1990, 73, 1359.
13. Gervay, J.; Nguyen, C.P.; Flaherty, T.M. J. Am. Chem. Soc. submitted.
14. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
15. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
16. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
17. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
18. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
19. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
20. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
21. Several different terms have been used to describe these compounds including carbopeptoids, saccharopeptides, and sugar amino acids. For leading articles see: Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575. Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 2549. Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425. Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 35, 2712. Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775. von Roedern, E.G.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687. Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887. Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
22. Dohi, T.; Nores, G.A.; Oguchi, H.; Inufusa, H.; Hakomori, S.-I. Gangliosides and Cancer edited by H.F. Oettgen VCH publishers, New York, NY 1989, pp. 273-282. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1984, 134, 229. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1981, 94, 193. Gross, S.J.; Williams, M.A.; McCluer, R.H. J. of Neurochemistry 1980, 1351. McGuire, E.J.; Binkley, S.B. Biochemistry 1964, 1248.
23. Dohi, T.; Nores, G.A.; Oguchi, H.; Inufusa, H.; Hakomori, S.-I. Gangliosides and Cancer edited by H.F. Oettgen VCH publishers, New York, NY 1989, pp. 273-282. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1984, 134, 229. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1981, 94, 193. Gross, S.J.; Williams, M.A.; McCluer, R.H. J. of Neurochemistry 1980, 1351. McGuire, E.J.; Binkley, S.B. Biochemistry 1964, 1248.
24. Dohi, T.; Nores, G.A.; Oguchi, H.; Inufusa, H.; Hakomori, S.-I. Gangliosides and Cancer edited by H.F. Oettgen VCH publishers, New York, NY 1989, pp. 273-282. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1984, 134, 229. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1981, 94, 193. Gross, S.J.; Williams, M.A.; McCluer, R.H. J. of Neurochemistry 1980, 1351. McGuire, E.J.; Binkley, S.B. Biochemistry 1964, 1248.
25. Dohi, T.; Nores, G.A.; Oguchi, H.; Inufusa, H.; Hakomori, S.-I. Gangliosides and Cancer edited by H.F. Oettgen VCH publishers, New York, NY 1989, pp. 273-282. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1984, 134, 229. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1981, 94, 193. Gross, S.J.; Williams, M.A.; McCluer, R.H. J. of Neurochemistry 1980, 1351. McGuire, E.J.; Binkley, S.B. Biochemistry 1964, 1248.
26. Dohi, T.; Nores, G.A.; Oguchi, H.; Inufusa, H.; Hakomori, S.-I. Gangliosides and Cancer edited by H.F. Oettgen VCH publishers, New York, NY 1989, pp. 273-282. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1984, 134, 229. Lifely, M.R.; Gilbert, A.S.; Moreno, C. Carbohydr. Res. 1981, 94, 193. Gross, S.J.; Williams, M.A.; McCluer, R.H. J. of Neurochemistry 1980, 1351. McGuire, E.J.; Binkley, S.B. Biochemistry 1964, 1248.
27. For examples see: Gervay, J.; Peterson, J.M.; Oriyama, O. Danishefsky, S.J. J. Org. Chem. 1993, 58, 5465. Danishefsky, S.J.; Koseki, K.; Griffith, D.A.; Gervay, J. Peterson, J.M.; McDonald, F.E.; Oriyama, T. J. Am. Chem. Soc. 1992, 114, 8331. Nicolaou, K.C.; Hummel, C.W.; Bockovich, N.J.; Wong, C.-H. J. Chem. Soc. Chem. Comm. 1991, 870. Numata, M.; Sugimoto, M.; Shibayama, S.; Ogawa, T. Carbohydr. Res. 1988, 174, 73.
28. For examples see: Gervay, J.; Peterson, J.M.; Oriyama, O. Danishefsky, S.J. J. Org. Chem. 1993, 58, 5465. Danishefsky, S.J.; Koseki, K.; Griffith, D.A.; Gervay, J. Peterson, J.M.; McDonald, F.E.; Oriyama, T. J. Am. Chem. Soc. 1992, 114, 8331. Nicolaou, K.C.; Hummel, C.W.; Bockovich, N.J.; Wong, C.-H. J. Chem. Soc. Chem. Comm. 1991, 870. Numata, M.; Sugimoto, M.; Shibayama, S.; Ogawa, T. Carbohydr. Res. 1988, 174, 73.
29. For examples see: Gervay, J.; Peterson, J.M.; Oriyama, O. Danishefsky, S.J. J. Org. Chem. 1993, 58, 5465. Danishefsky, S.J.; Koseki, K.; Griffith, D.A.; Gervay, J. Peterson, J.M.; McDonald, F.E.; Oriyama, T. J. Am. Chem. Soc. 1992, 114, 8331. Nicolaou, K.C.; Hummel, C.W.; Bockovich, N.J.; Wong, C.-H. J. Chem. Soc. Chem. Comm. 1991, 870. Numata, M.; Sugimoto, M.; Shibayama, S.; Ogawa, T. Carbohydr. Res. 1988, 174, 73.
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33. Gervay, J.; Mamuya, N.M. Tetrahedron Lett. submitted.
34. Ratcliff, M.R.; Venot, A.P.; Abbas, Z.S.; Eur. Pat. Appl. EP 319,253 (Chem. Abstr. 1990, 112, 175281a).
35. Yield based upon recovered starting material.
36. Li, Y.-Y. Dept. of Biochemistry, Tulane University School of Medicine, New Orleans, LA 70112, personal communication.
37. Recent investigations in our laboratories indicate that addition of benzhydryl amine is orders of magnitude faster than that of the glycinyl amine.