Preparation of a protected triamino analogue of cholic acid and sequential incorporation of amino acids in solution and on a solid support.
We have prepared a triamine derivative of cholic acid with protecting groups on the amines that allow sequential amide formation. The triamine was formed from 3 alpha,7 alpha, 12 alpha-trihydroxycholan-24-ol with good stereoselectivity. Sequential removal of the amine protecting groups and amide formation was achieved in high-yielding steps and was performed in solution and on a solid support.
Zhou
X T
XT
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602, USA.
Rehman
A
A
Li
C
C
Savage
P B
PB
D000577:Amides / Q000138:chemical synthesis; D000596:Amino Acids / Q000737:chemistry*; D002793:Cholic Acids / Q000138:chemical synthesis*; D005449:Fluorenes / Q000737:chemistry; D005563:Formic Acid Esters / Q000737:chemistry; D012996:Solutions; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D000577:Amides; D000596:Amino Acids; D002793:Cholic Acids; D005449:Fluorenes; D005563:Formic Acid Esters; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids; D012996:Solutions; C000345:t-butyloxycarbonyl group