Document Detail

Differentially-protected steroidal triamines; scaffolds with potential for medicinal, supramolecular, and combinatorial chemistry.
MedLine Citation:
PMID:  15534710     Owner:  NLM     Status:  MEDLINE    
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.
Vicente del Amo; Laura Siracusa; Theodoros Markidis; Beatriz Baragaña; Khadga M Bhattarai; Marta Galobardes; Gregorio Naredo; M Nieves Pérez-Payán; Anthony P Davis
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2004-10-15
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  2     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2004 Nov 
Date Detail:
Created Date:  2004-11-09     Completed Date:  2006-06-22     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  3320-8     Citation Subset:  IM    
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
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MeSH Terms
Amino Acids / chemistry
Azides / chemistry
Chemistry, Organic / methods*
Cholic Acid / chemistry*
Combinatorial Chemistry Techniques
Molecular Structure
Polyamines / chemical synthesis*,  chemistry
Reg. No./Substance:
0/Amino Acids; 0/Azides; 0/Polyamines; 81-25-4/Cholic Acid

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