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Solid-phase organik syntheses - Burdges K.

Burdges K. Solid-phase organik syntheses - John Wiley & Sons, 2000. - 283 p.
ISBN 0-471-22824-9
Download (direct link): phaseorganicsynthesis2000.pdf
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1.6. CONCLUSION 19
H H
so2nh2 N N
' BOCNK^ -^NHBOC iprNEbMeph
PF
Me
22
110C
H
BOCN N ~Y N N H BOC

J

() hydrolysis
N /
co2Et couple to resin
(iii) peptide coupling
H H
.l\L /Ns
peptide-NhT^^ v"n/"^v'NH-peptide
Nv ,P CF3S03H/PhSMe

H
Nx>

H H
peptide-N -^44^ ^"y" ^N H-peptide NH2+X'
Scheme 23.
1.6. CONCLUSION
No single approach will be universally the best for preparations of guanidines of all types. Of the methods that involve supported guanylating reagents, those of Dodd and Wallace and of Josey et al. (Schemes 16 and 15, respectively) seem to be particularly useful. Solid-phase syntheses of guanidines in which the guanylating reagent is in solution have been explored less than the ajternative strategy and appear to have some merit. Indeed, a very recent paper has compared solid-phase syntheses of oligomeric guanidines by various routes and concludes that the best method
20 SOLID-PHASE SYNTHESES OF GUANIDINES
is via reaction of resin bound amines with thioureas activated with EDC {1 (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride} .51
REFERENCES
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2. Carpenter, R.; Anchin, J. .; Linthicum, D. S. Molecular Probes for Sweetness: Immunorecognition of Superpotent Guanidinium Compounds, Hybri-doma 1996, 75, 17-21.
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4. Bosin, T. R.; Hanson, R. N.; Rodricks, J. V.; Simpson, R. A.; Rapoport, H. Routes to Functionalized Guanidines. The Synthesis of Guanidino Diesters, J. Org. Chem. 1973, 38, 1591-1600.
5. Nagarajan, S.; Ho, T. L.; DuBois, G. E. A Simple Method for Synthesis of Unsymmetrical Trisubstituted Guanidines, Synth. Commun. 1992,22, 1191 1198.
6. Stark, H.; Krause, .; Arrang, J.-M.; Ligneau, X.; Schwartz, J.-C.; Schunack, W. Unsymmetrically Substituted Guanidines as Potent Histamine -Receptor Antagonists, Bioorg. Med. Chem. Lett. 1994, 4, 2907-2912.
7. Barker, P. L.; Gendler, R L.; Rapoport, H. Acylation of Dibasic Compounds Containing Amino Amidine and Aminoguanidine Functions, J. Org. Chem. 1981, 46,2455-2465.
8. Webb, T. R.; Eigenbrot, C. Conformationally Restricted Arginine Analogues, J. Org. Chem. 1991, 56, 3009-3016.
9. Reddy, N. L.; Hu, L.-Y.; Cotter, R. E.; Fischer, J. B.; Wong, W. J.; McBurney, R. N.; Weber, E.; Holmes, D. L.; Wong, S. .; Prasad, R.; Keana, J. F. W. Synthesis and Structure-Activity Studies of A^N'-Diarylguanidine Derivatives. A^-(l-Naphthyl)-,/V'-(3-ethylphenyl)-yV'-methylguanidine: A New, Selective Noncompetitive NMDA Receptor Antagonist, J. Med. Chem. 1994,
37, 260-267.
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11. Rasmussen, C. R.; Villani, F. J. Jr.; Reynolds, . E.; Plampin, J. N.; Hood, A. R.; Hecker, L. R.; Nortey, S. O.; Hanslin, A.; Costanzo, M. J.; Howse, R.
REFERENCES 21
M. Jr.; Molinari, A. J. A Versatile Synthesis of Novel TV, Af,yV'-Trisubstituted Guanidines, Synthesis 1998, 460-466.
12. Lai, B.; Gangopadhyay, A. K. A Practical Synthesis of Free and Protected Guanidino Acids from Amino Acids, Tetrahedron Lett. 1996, 37, 24832486.
13. Sulikowski, .; Kim, K.; Sulikowski, G. A.; Nagarjan, S.; Linthicum, D. S. Ligands for the Study of Sweet Taste Receptors: Synthesis of Fluorescent A^N'-disubstituted Guanidineacetic Acids, Bioorg. Med. Chem. Lett. 1995,
5, 2875-2878.
14. Nagarajan, S.; Kellogg, M. S.; DuBois, G. E.; Williams, D. S.; Gresk, C. J.; Markos, C. S. Understanding the Mechanism of Sweet Taste: Synthesis of Tritium Labeled Guanidineacetic Acid, J. Labelled Compounds and Radio-pharmaceut. 1992, 31, 599-607.
15. Corey, E. J.; Ohtani, M. Enantiospecific Synthesis of a Rigid C2 Symmetric, Chiral Guanidine by a New and Direct Method, Tetrahedron Lett. 1989, 30, 5227-5230.
16. Lammin, S. G.; Pedgrift, B. L.; Ratcliffe, A. J. Conversion of Anilines to Bis-Boc Protected N-Methylguanidines, Tetrahedron Lett. 1996, 37, 6815 6818.
17. Atwal, K. S.; Ahmed, S. Z.; OReilly, . C. A Facile Synthesis of Cy-anoguanidines from Thioureas, Tetrahedron Lett. 1989, 30, 7313-7316.
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