Method for preparing isofagomine and its derivatives
View Patent ↗A method for preparing isofagomine, its derivatives, intermediates and salts thereof using novel processes to make isofagomine from D-(−)-arabinose and L-(−)-xylose.
1. A compound of the formula
where PG is a hydroxyl protecting group.
2. The compound of claim 1 , wherein PG is benzyl.
3. A method for preparing isofagomine, a protected isofagomine salt, or an isofagomine acid salt comprising converting the compound of any one of claims 1 to 2 to make isofagomine, a protected isofagomine salt, or an isofagomine acid salt thereof, wherein the conversion comprises:
(i) reducing the compound to a triprotected primary amine; deprotecting the primary amine to a diol; and catalytically hydrogenating the diol; or
(ii) converting the compound to a protected diol and deprotecting the diol; or
(iii) converting the compound to a protected isofagomine salt.
4. The method of claim 3 , wherein converting the compound of the formula
to make isofagomine, a protected isofagomine salt, or an isofagomine acid salt comprises reducing the compound to a triprotected primary amine; deprotecting the primary amine to a diol; and catalytically hydrogenating the diol optionally in the presence of an acid.
5. The method of claim 3 , wherein converting the compound of the formula
to make isofagomine, a protected isofagomine salt, or an isofagomine acid salt comprises converting the compound to a protected diol and deprotecting the diol.
6. The method of claim 3 , wherein the compound of the formula
is converted to a protected isofagomine salt.
7. The method of claim 6 , further comprising deprotecting the protected isofagomine salt.