Synthesis of sphingosines and their derivatives
Embodiments of the present disclosure provide for methods of making sphingosines and derivatives thereof, and the like.
1. A method of making a compound of formula V,
comprising reacting a compound of formula III,
with an compound of formula IV,
under conditions such that a compound of formula V is formed, wherein
n is 0 to 50;
MX n′ is B(OH) 2 ;
R 1 is H or a protecting group comprising a carbonyl group;
R 2 is a protecting group comprising a carbonyl group;
R 3 is selected from H, an alkyl, substituted alkyl, aryl, substituted aryl, heterocycle, or a substituted heterocycle; and
R 4 is a protecting group, wherein the protecting group comprises a group selected from the list consisting of a silyl group, an ester group, an acetal group, a carbonate group, a glycoyl group, a phosphoryl group, and an ether group.
2. The method of claim 1 , wherein n is 12.
3. The method of claim 1 , wherein R 1 is H.
4. The method of claim 1 , wherein R 2 is t-butoxycarbonyl (Boc), a benzyloxycarbonyl (Cbz), or a 9-fluorenylmethoxycarbonyl (Fmoc).
5. The method of claim 1 , wherein R 3 is a phenyl.
6. The method of claim 1 , wherein R 4 is a tert-butyldimethylsilyl, triisopropylsilyl, or tert-butyldiphenylsilyl.
7. A method of making a compound of formula V,
comprising reacting a compound of formula III,
with an alkyenylstannane under conditions such that a compound of formula V is formed, wherein
n is 0 to 50;
R 1 is H or a protecting group comprising a carbonyl group;
R 2 is a protecting group comprising a carbonyl group;
R 3 is selected from H, an alkyl, substituted alkyl, aryl, substituted aryl, heterocycle, or a substituted heterocycle; and
R 4 is a protecting group, wherein the protecting group comprises a group selected from the list consisting of a silyl group, an ester group, an acetal group, a carbonate group, a glycoyl group, a phosphoryl group, and an ether group.
8. A method of making a compound of formula VIII,
comprising,
a) reacting a compound of formula V as in claim 1 with a reducing agent under conditions such that a compound of formula VI is formed,
and
b) reacting a compound of formula VI with an acid, base, or hydrogen under conditions such that a compound of formula VIII is formed.