Back to results
US 2023/0399338 A1Published application
METHOD OF SYNTHESIZING (3S,3AR,5R,7AS,8S)- HEXAHYDRO-4H-3,5-METHANOFURO[2,3-b]PYRAN-8-OL
AssigneePurdue Research Foundation
InventorsArun K. Ghosh, Shivaji Markad
Life of this patent
Estimating the term…
Abstract
The disclosure relates to a method of synthesizing the high-affinity, non-petidyl ligand (3S,3aR,5R,7aS,8S)-hexahydro-4H-3,5-methanofuro[2,3-b]pyran-8-ol, which is useful in the synthesis of various compounds, such as HIV-1 protease inhibitors.
Claims20
A method of making a compound of the formula (I):
- or a salt thereof, with an enantiomeric excess (ee) of at least 90%;
- wherein:
- X1 is alkylene, —O—, —CH2NR1— or —NHR1—, wherein R1 is alkyl, aryl or heteroaryl, and
- R2 is hydroxy, alkoxy or amido;
- the method comprising
- (i) converting a compound of the formula (II):
- or a salt thereof,
- to a compound of the formula (III):
- or a salt thereof;
- (ii) converting the compound of formula (III), or a salt thereof, to a compound of the formula (IV):
- or a salt thereof;
- and
- (iii) converting the compound of formula (IV), or a salt thereof, to the compound of the formula (I).
10 more elements
A method of making a compound of the formula (VI):
- or a salt thereof, with an enantiomeric excess (ee) of at least 90%;
- wherein:
- X1 is alkylene, —O—, —CH2NR1— or —NHR1—, wherein R1 is alkyl, aryl or heteroaryl;
- the method comprising:
- (i) converting a compound of the formula (I):
- or a salt thereof,
- wherein:
- X1 is alkylene, —O—, —CH2NR1— or —NHR1—, wherein R1 is alkyl, aryl or heteroaryl, and
- R2 is hydroxy, alkoxy or amido,
- to a compound of the formula (VII):
- or a salt thereof, wherein X2 is O or CH2;
- and
- (ii) converting the compound of formula (VII), or a salt thereof, to a compound of the formula (VI), or a salt thereof.
10 more elements
A method of making a compound of the formula (VIII):
- or a salt thereof, with an enantiomeric excess (ee) of at least 90%;
- wherein:
- X1 is alkylene, —O—, —CH2NR1— or —NHR1—, wherein R1 is alkyl, aryl or heteroaryl, and
- R3 is hydroxyalkyl or COR2, wherein R2 is hydroxy, alkoxy or amido;
- the method comprising:
- (i) converting a compound of the formula (I):
- or a salt thereof,
- wherein:
- X1 is alkylene, —O—, —CH2NR1— or —NHR1—, wherein R1 is alkyl, aryl or heteroaryl;
- and
- R2 is hydroxy, alkoxy or amido,
- to a compound of the formula (VIII).
9 more elements
Dependencies are inferred from the claim text.