Synthesis of azide-alkyne fragments for "Click" chemical applications. Part 2. Formation of oligomers from orthogonally protected chiral trialkylsilylhomopropargyl azides and homopropargyl alcohols

Journal of Organic Chemistry

Volumn 75, Issue 2, 2010, Pages 390-398

  Montagnat, Oliver D ^a   Lessene, Guillaume ^b   Hughes, Andrew B ^a  

^a LA TROBE UNIVERSITY   (Australia)

^b WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL APPLICATIONS; CHEMICAL EQUATIONS; DIPOLAR CYCLOADDITIONS; L-AMINO ACIDS; PEPTIDOMIMETICS; PROPARGYL ALCOHOL;

ACETYLENE; AMINO ACIDS; CYCLOADDITION; OLIGOMERS; ORGANIC ACIDS;

NITROGEN COMPOUNDS;

ALCOHOL DERIVATIVE; ALKYNE; AMINO ACID; AMINO ACID DERIVATIVE; AZIDE; OLIGOMER; PEPTIDOMIMETIC AGENT; TRIAZOLE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; PROPANOLS; STEREOISOMERISM;

EID: 75349105472     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9021887     Document Type: Article

References (25)

1. For selected reviews on "click" chemistry see: Kolb, H. C.; Finn, M. G.; Sharpless,K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
2. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137.
3. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51-68.
4. Montagnat, O. D.; Lessene, G.; Hughes, A. B. Tetrahedron Lett. 2006, 47, 6971-6974.
5. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071-13072.
6. 3-1,4-disubstituted-triazole scaffold" is defined by repeating units of a 1,2,3-triazole ring, substituted with 2-carbon chains attached to N-1 and C-4 of the 1,2,3-triazole ring. Each 2-carbon chain is substituted with an R group, which is attached to the carbon positioned adjacent to N-1 of the 1,2,3-triazole ring.
7. Koppenhoefer, B.; Schurig, V. Org. Synth. 1988, 66, 151-159.
8. Koppenhoefer, B.; Schurig, V. Org. Synth. 1988, 66, 160-172.
9. 13C NMR spectroscopy revealed no other diastereoisomers were present, and thus chiral purity had been maintained.
10. Fisher, C.; Morse, E.; Romer, B.; You, T.; Mosher, C.; Mosher, H. Tetrahedron 1992, 48, 2993-3000.
11. Pazdzioch, W.; Myszkowski, J.; Goc, W. Pol. J. Appl. Chem. 1993, 36, 335-343.
12. Mills, F. D.; Brown, R. T. Synth. Commun. 1990, 20, 3131-3135.
13. Vasanthakumar, G. P.; Gopi, H. N.; Suresh Babu, V. V. Protein Pept. Lett. 2002, 9, 529-532.
14. Kim, S.; Lee, W. J. I. Bull. Korean Chem. Soc. 1984, 5, 187-190.
15. Cramer, F. Angew. Chem. 1960, 72, 236-249.
16. Greene, T. W.; Wutz, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley-Interscience Publications: New York, 1999.
17. Chersi, A.; Giommi, S.; Rosano, L. Biochim. Biophys. Acta 2000, 2, 196-200.
18. Markgraf, J. H.; Davis, H. A. J. Chem. Educ. 1990, 67, 173-174.
19. Cai, X.; Chorghade, M. S.; Fura, A.; Grewal, G. S.; Jaregui, K. A.; Lounsbury, H. A.; Scannell,R. T.; Yeh, C. G.; Young, M. A.; YuLiang Guo, S.; Moriarty, R. M.; Penmasta, R.; Rao, M. S.; Singhal, R. K.; Song, Z.; Staszewski, J. P.; Tuladar, S. M.; Yang, S. Org. Proc. Res. Dev. 1999, 3, 73-76.
20. Ho, P.; Davies, N. Synthesis 1983, 462.
21. Padwa, A. 1,3-Dipolar Cycloaddition Chemistry, 1st ed. John Wiley & Sons Inc.: New York, 1984; Vol. 1.
22. 3-substituted homotetramer possessing only isobutyl side chains would determine if this variation is a contributing factor.
23. The conformation of the initial 2D structure was based on the rationale that the side chain substituents of the oligomeric, 1,4-disubstituted-1,2,3- triazole backbone chain would be oriented trans to each other, while the 1,2,3-triazole rings of the backbone chain would also be oriented trans to each other. As such, only one local energy minimum was calculated.
24. Angelo, N. G.; Arora, P. S. J. Am. Chem. Soc. 2005, 127, 17134-17135.
25. Hanessian, S.; Luo, X.; Schaum, R.; Michnick, S. J. Am. Chem. Soc. 1998, 120, 8569-8570.