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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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so2nh2 N N
' BOCNK^ -^NHBOC iprNEbMeph


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


peptide-N -^44^ ^"y" ^N H-peptide NH2+X'
Scheme 23.
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
is via reaction of resin bound amines with thioureas activated with EDC {1 (3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride} .51
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