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Org Biomol Chem ; 2(22): 3320-8, 2004 Nov 21.
Article in English | MEDLINE | ID: mdl-15534710

ABSTRACT

Cholic acid 2a has been converted into two new orthogonally-protected triamino scaffolds, 13 and 14. The synthesis proceeds via the bis-Boc-NH-substituted azide 10, for which an improved preparation is described. After removal of the Boc groups, the two axial amines are differentiated through a novel monoprotection employing 1-(2-nitrobenzenesulfonyloxy)-benzotriazole 29. Regioselectivity of > or 50 : 1 is achieved, presumably reflecting an exceptional sensitivity to steric hindrance. Protection of the remaining amino group as Boc or Alloc gives the scaffolds in approximately 40% overall yield from cholic acid. Scaffold 13 has been sequentially deprotected and derivatised with N-carbamoyl amino acids, to give a model for tripodal peptide libraries.


Subject(s)
Chemistry, Organic/methods , Cholic Acid/chemistry , Polyamines/chemical synthesis , Amino Acids/chemistry , Azides/chemistry , Combinatorial Chemistry Techniques , Molecular Structure , Polyamines/chemistry , Stereoisomerism
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