Expedient synthesis of triazole-linked glycosyl amino acids and peptides

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3123-3126

  Kuijpers, Brian H M ^a   Groothuys, Stan ^a   Keereweer, A R ^a   Quaedflieg, Peter J L M ^b   Blaauw, Richard H ^c   Van Delft, Floris L ^a   Rutjes, Floris P J T ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^b DSM RESEARCH   (Netherlands)

^c CHIRALIX B V   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AMINO ACID DERIVATIVE; AZIDE; COPPER; GLYCOPEPTIDE; GLYCOSIDE; PEPTIDE; TRIAZOLE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CYCLOADDITION;

AMINO ACIDS; CATALYSIS; COPPER; GLYCOPEPTIDES; GLYCOSIDES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 4544344028     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048841o     Document Type: Article

References (43)

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8. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
9. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
10. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
11. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
12. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
13. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
14. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
15. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
16. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
17. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
18. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
19. For entries into C-glyco amino acid synthesis, see for example: (a) Taylor, C. M. Tetrahedron 1998, 54, 11317. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395. (d) Vincent, S. P.; Schleyer, A.; Wong, C.-H. J. Org. Chem. 2000, 65, 4440. (e) Xu, X.; Fakha, G.; Sinou, D. Tetrahedron 2002, 58, 7539. (f) Lane, J. W.; Halcomb, R. L. J. Org. Chem. 2003, 68, 1348 (g) Turner, J. J.; Leeuwenburgh, M. A.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron 2001, 42, 8713. (h) Dondoni, A.; Mariotti, G.; Marra, A.; Massi, A. Synthesis 2001, 14, 2129. (i) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375. (j) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591. (k) Dondoni, A.; Giovannini, P. P.; Marra, A. J. Chem. Soc., Perkin Trans. 1 2002, 2380. (l) Nolen, E. G.; Kurish, A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449. (m) Palomo, C.; Oiarbide, M.; Landa, A.; Concepción González-Rego, M.; García, J. M.; Gonzáles, A.; Odriozola, J. M.; Martín-Pastor, M.; Linden, A. J. Am. Chem. Soc. 2002, 124, 8637.
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22. For earlier reports on [3 + 2] cycloadditions of azidoglycosides and acetylenes, see: (a) Bröder, W.; Kunz, H. Carbohydr. Res. 1993, 249, 221. (b) Al-Masoudi, N. A.; Al-Soud, Y. A. Tetrahedron Lett. 2002, 43, 4021. (c) Marco-Contelles, J.; Jiménez, C. A. Tetrahedron 1999, 55, 10511 (d) Peto, C.; Batta, G.; Gyorgydeak, Z.; Sztaricskai, F. Carbohydr. Chem. 1996, 15, 465 and references therein
23. For earlier reports on [3 + 2] cycloadditions of azidoglycosides and acetylenes, see: (a) Bröder, W.; Kunz, H. Carbohydr. Res. 1993, 249, 221. (b) Al-Masoudi, N. A.; Al-Soud, Y. A. Tetrahedron Lett. 2002, 43, 4021. (c) Marco-Contelles, J.; Jiménez, C. A. Tetrahedron 1999, 55, 10511 (d) Peto, C.; Batta, G.; Gyorgydeak, Z.; Sztaricskai, F. Carbohydr. Chem. 1996, 15, 465 and references therein
24. For earlier reports on [3 + 2] cycloadditions of azidoglycosides and acetylenes, see: (a) Bröder, W.; Kunz, H. Carbohydr. Res. 1993, 249, 221. (b) Al-Masoudi, N. A.; Al-Soud, Y. A. Tetrahedron Lett. 2002, 43, 4021. (c) Marco-Contelles, J.; Jiménez, C. A. Tetrahedron 1999, 55, 10511 (d) Peto, C.; Batta, G.; Gyorgydeak, Z.; Sztaricskai, F. Carbohydr. Chem. 1996, 15, 465 and references therein
25. For earlier reports on [3 + 2] cycloadditions of azidoglycosides and acetylenes, see: (a) Bröder, W.; Kunz, H. Carbohydr. Res. 1993, 249, 221. (b) Al-Masoudi, N. A.; Al-Soud, Y. A. Tetrahedron Lett. 2002, 43, 4021. (c) Marco-Contelles, J.; Jiménez, C. A. Tetrahedron 1999, 55, 10511 (d) Peto, C.; Batta, G.; Gyorgydeak, Z.; Sztaricskai, F. Carbohydr. Chem. 1996, 15, 465 and references therein
26. For examples of biologically active triazoles, see: (a) Alvarez, R.; Velazquez, S.; San, F.; Aquaro, S.; De, C.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185. (b) Velazquez, S.; Alvarez, R.; Perez, C.; Gago, F.; De, C.; Balzarini, J.; Camarasa, M. J. Antivir. Chem. Chemother. 1998, 9, 481. (c) Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953.
27. For examples of biologically active triazoles, see: (a) Alvarez, R.; Velazquez, S.; San, F.; Aquaro, S.; De, C.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185. (b) Velazquez, S.; Alvarez, R.; Perez, C.; Gago, F.; De, C.; Balzarini, J.; Camarasa, M. J. Antivir. Chem. Chemother. 1998, 9, 481. (c) Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953.
28. For examples of biologically active triazoles, see: (a) Alvarez, R.; Velazquez, S.; San, F.; Aquaro, S.; De, C.; Perno, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J. J. Med. Chem. 1994, 37, 4185. (b) Velazquez, S.; Alvarez, R.; Perez, C.; Gago, F.; De, C.; Balzarini, J.; Camarasa, M. J. Antivir. Chem. Chemother. 1998, 9, 481. (c) Genin, M. J.; Allwine, D. A.; Anderson, D. J.; Barbachyn, M. R.; Emmert, D. E.; Garmon, S. A.; Graber, D. R.; Grega, K. C.; Hester, J. B.; Hutchinson, D. K.; Morris, J.; Reischer, R. J.; Ford, C. W.; Zurenko, G. E.; Hamel, J. C.; Schaadt, R. D.; Stapert, D.; Yagi, B. H. J. Med. Chem. 2000, 43, 953.
29. Enantiopure propargylglycine is commercially available but in our hands was prepared via an enzymatic resolution process: (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000; p 23.
30. Enantiopure propargylglycine is commercially available but in our hands was prepared via an enzymatic resolution process: (a) Wolf, L. B.; Sonke, T.; Tjen, K. C. M. F.; Kaptein, B.; Broxterman, Q. B.; Schoemaker, H. E.; Rutjes, F. P. J. T. Adv. Synth. Catal. 2001, 343, 662. (b) Sonke, T.; Kaptein, B.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Formaggio, F.; Toniolo, C.; Rutjes, F. P. J. T.; Schoemaker, H. E. In Stereoselective Biocatalysis; Patel, R. N., Ed.; Marcel Dekker: New York, 2000; p 23.
31. Shiozaki, M.; Arai, M.; Macindoe, W. M.; Mochizuki, T.; Kurakata, S.; Maeda, H.; Nishijima, M. Chem. Lett. 1996, 9, 735
32. Prepared from 2,3,4,6-tetra-O-benzylglucose by treatment with DBU and DPPA: Mizuno, M.; Shioiri, T. Chem. Commun. 1997, 2165.
33. 3: Lehnhoff, S.; Goebel, M.; Karl, R. M.; Kloesel, R.; Ugi, I. Angew. Chem., Int. Ed. 1995, 34, 1104.
34. 3, respectively.
35. Prepared from the corresponding glucosamine via azido transfer, followed by acetylation: Alper, P. B.; Hung, S.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029.
36. 3 in MeOH, 4 h, rt; 1.25 M aqueous NaOH, 24 h, reflux.
37. van Esseveldt, B. C. J.; van Delft, F. L.; de Gelder, R.; Rutjes, F. P. J. T. Org. Lett. 2003, 5, 1717.
38. Prepared from Boc-protected (S)-propargylglycine amide via dehydration: Cossu, S.; Giacomelli, G.; Conti, S.; Falorni, M. Tetrahedron 1994, 50, 5083.
39. Dipeptides 34 and 35 were synthesized using a standard coupling reaction involving PyBOP.
40. 8
41. Dondoni, A.; Mariotti, G.; Marra, A. J. Org. Chem. 2002, 67, 4475.
42. (a) Rosenberg, S. H.; Spina, K. P.; Woods, K. W.; Polakowski, J.; Martin, D. L.; Yao, Z. L.; Stein, H. H.; Cohen, J.; Barlow, J. L.; Egan, D. A.; Tricarico, K. A.; Baker, W. R.; Kleinert, H. D. J. Med. Chem. 1993, 36, 449.
43. (b) Lundquist, J. T.; Pelletier, J. C. Org. Lett. 2001, 3, 781.