Methods and intermediates for synthesizing SK1-I
The invention provides methods for synthesizing the compound (2R,3S,4E)-N-methyl-5-(4′-pentylphenyl)-2-aminopent-4-ene-1,3-diol, also known as SK1-I, and intermediate compounds used in its synthesis.
1. A method for synthesizing the compound
in which R is an alkyl group, comprising the reaction steps of:
(i)
(ii)
(iii)
(iv)
wherein R is a C 1-20 alkyl group;
(v)
(vi)
and
(vii) reacting
with DIBAL in the presence of Rochelle salt, thereby obtaining
2. The method of claim 1 , wherein R is a linear alkyl group.
3. The method of claim 1 , wherein R is a branched alkyl group.
4. The method of claim 1 , wherein step (vii) comprises the substeps of:
(a) adding
to DIBAL to form a reaction mixture, and
(b) adding the reaction mixture to a solution comprising Rochelle salt.
5. The method of claim 4 , wherein R is a linear alkyl group.
6. The method of claim 5 , wherein R is a C 5 H 11 group.
7. The method of claim 4 , wherein R is a branched alkyl group.