(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-2-one synthesis

13synthesis methods

Product Name:(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-2-one
CAS Number:60623-67-8
Molecular formula:C15H22O4
Molecular Weight:266.3328

36969-89-8
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62961-72-2 Synthesis

2H-Cyclopenta[b]furan-4-carboxaldehyde, hexahydro-5-hydroxy-2-oxo-, (3aR,4R,5R,6aS)-

62961-72-2
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(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-2-one

60623-67-8
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Yield:60623-67-8 87%

Reaction Conditions:

Stage #1: dimethyl 2-oxoheptylphosphonatewith potassium hexamethylsilazane in tetrahydrofuran at -78; for 0.5 h;Inert atmosphere;
Stage #2: Corey aldehyde in tetrahydrofuran at 20; for 4 h;Temperature;Reagent/catalyst;

Steps:

1.2; 2.2; 3.2; 4.2; 5.2; 6.2; 7.2; 8.2; 9.2 (2) Synthesis of compound 3

Suspend dimethyl (β-oxoheptyl)phosphonate (10g, 45mmol) in anhydrous THF (50mL) under nitrogen protection at -78°C, and mix KHMDS (45mL, 45mmol, 1M) in THF (100mL) solution Add dropwise to the above suspension. After stirring at -78°C for 30 min, a solution of compound 2 (3.8 g, 22 mmol) in THF (20 mL) was slowly added dropwise to the above suspension. Then, the reaction temperature was slowly raised to room temperature, and the reaction was stirred for 4 hours. After the reaction is complete, add saturated NH4Cl solution (50mL) to quench the reaction, extract with ethyl acetate (200mL×3), combine the organic phases, wash with saturated brine, dry with anhydrous Na2SO4, filter, concentrate, and separate and purify by column chromatography to obtain Light yellow oil (6.9 g, 87%).

References:

CN111777537,2020,A Location in patent:Paragraph 0090; 0094-0096; 0118; 0122-0124; 0146; 0150-0152

32233-40-2 Synthesis