A photoreactive analogue of the immunosuppressant FTY720.
An azido group was incorporated into the immunomodulatory agent FTY720, accomplishing the first synthesis of a photoactivatable analogue of this ligand (2) in 9 steps from 2-(4-hydroxyphenyl)ethanol and in 34% overall yield. The key steps are formation of a primary amine at a quaternary center of aniline derivative 13 followed by selective diazotization of the arylamine.
Sun
Chaode
C
Department of Chemistry and Biochemistry, Queens College of The City University of New York, Flushing, New York 11367-1597, USA.
Bittman
Robert
R
D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry*; D000068876:Fingolimod Hydrochloride; D007166:Immunosuppressive Agents / Q000138:chemical synthesis / Q000737:chemistry*; D010777:Photochemistry; D011412:Propanolamines / Q000138:chemical synthesis / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry
C516082:2-(3-azido-4-octylphenethyl)-2-aminopropane-1,3-diol; D001386:Azides; D007166:Immunosuppressive Agents; D011412:Propanolamines; D011409:Propylene Glycols; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine