Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Cuilleron, C.Y. et al.

Synthesis and stereochemistry of 7 beta- and 7 alpha-amino-, acetamido-, hemisuccinamido- and terephthalamido derivatives of testosterone.

The reduction of 3-ethylenedioxy-7-oximino-5-androsten-17 beta-yl acetate and of its 17 beta-tetrahydropyranyl ether analog with sodium in ethanol, followed by thin-layer chromatography, allowed the isolation of the corresponding 17 beta-hydroxy- and 17 beta-tetrahydropyranyloxy-5-en-7 beta- and 7 alpha-amines which were also characterized as 7-acetamides. The acylation of the two epimeric 17 beta-hydroxy-5-en-7-amines with succinic anhydride followed by selective saponification of the 17 beta-hemisuccinate group and diazomethane esterification, gave the corresponding 17 beta-hydroxy-5-en-7 beta- and 7 alpha-hemisuccinamido methyl esters characterized also as 17 beta-acetates. On the other hand, the acylation of the two 17 beta-tetrahydropyranyloxy-5-en-7-amines with the acid chloride of terephthalic acid monomethyl ester led to the more rigid 7 beta- and 7 alpha-terephthalamido methyl ester side-chains. The acidolysis of the 3-ethyleneketal protecting group of the preceding 5-en-7-N-acyl derivatives regenerated the 4-en-3-oxo function while the 17 beta-tetrahydropyranyl ether group was cleaved simultaneously into the 17 beta-alcohol. The four desired 7 beta- and 7 alpha-hemisuccinamido- and terephthalamido carboxylic side-chain derivatives of 17 beta-hydroxy-4-androsten-3-one (testosterone) were finally obtained by saponification of the corresponding methyl esters.[1]

References

Synthesis and stereochemistry of 7 beta- and 7 alpha-amino-, acetamido-, hemisuccinamido- and terephthalamido derivatives of testosterone. Cuilleron, C.Y., Mappus, E., Forest, M.G., Bertrand, J. Steroids (1981) [Pubmed]

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