Abstract
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.
Publication types
-
Research Support, N.I.H., Extramural
MeSH terms
-
Azides / chemical synthesis
-
Azides / chemistry*
-
Fingolimod Hydrochloride
-
Immunosuppressive Agents / chemical synthesis
-
Immunosuppressive Agents / chemistry*
-
Photochemistry
-
Propanolamines / chemical synthesis
-
Propanolamines / chemistry*
-
Propylene Glycols / chemistry*
-
Sphingosine / analogs & derivatives*
-
Sphingosine / chemistry
Substances
-
2-(3-azido-4-octylphenethyl)-2-aminopropane-1,3-diol
-
Azides
-
Immunosuppressive Agents
-
Propanolamines
-
Propylene Glycols
-
Fingolimod Hydrochloride
-
Sphingosine