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Short Synthesis of Orthogonally Protected 3α,12α‐Diamino‐5β‐cholan‐24‐oic Acid, a Dipodal Steroid Scaffold for Combinatorial Chemistry
Author(s) -
Verzele Dieter,
Madder Annemieke
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600972
Subject(s) - chemistry , moiety , steroid , combinatorial chemistry , derivative (finance) , diastereomer , peptide , oxime , stereochemistry , organic chemistry , biochemistry , economics , hormone , financial economics
A short, practical, multigram‐scale synthesis of C3α‐NHAlloc, C12α‐NHBoc‐diamino‐5β‐cholan‐24‐oic acid 2 was developed, applying a new, straightforward synthetic strategy. Key features are the conservation of the carboxyl moiety at C24 during oxime reduction, the late differentiation between the C3 and C12 amino groups and the gradual separation of diastereomers during the synthesis. This orthogonally protected diamino steroid derivative can be used as starting point for the generation of steroid based dipodal peptide and non‐peptide combinatorial libraries. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)