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41639-74-1

Basic Information
CAS No.: 41639-74-1
Name: HYDRIDE-L
Article Data: 13
Molecular Structure:
Molecular Structure of 41639-74-1 (HYDRIDE-L)
Formula: C18H22O4
Molecular Weight: 302.37
Synonyms: 2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-(3-hydroxy-5-phenyl-1-pentenyl)-, [3aR-[3aa,4a(1E,3S*),5b,6aa]]-;2H-Cyclopenta[b]furan-2-one,hexahydro-5-hydroxy-4-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-,(3aR,4R,5R,6aS)- (9CI);PGX 9;
Density: 1.287 g/cm3
Boiling Point: 509.18 °C at 760 mmHg
Flash Point: 185.604 °C
PSA: 66.76000
LogP: 1.84880
Synthetic route

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

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one With chlorobis(2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane In tetrahydrofuran at -40℃; for 12h;
Stage #2: With hydrogenchloride In water at 20℃; for 0.5h; Reagent/catalyst; Temperature;
88%
With C20H35B In tetrahydrofuran; hexane at -40℃; for 12h;76%
55444-68-3

(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With potassium carbonate In methanol at 25℃; for 2h;83%
With methanol; potassium carbonate deprotection;
41639-73-0

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With methanol; potassium carbonate80%
With potassium carbonate In tetrahydrofuran; methanol for 2.5h;
Stage #1: (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one With methanol; potassium carbonate at 20 - 30℃;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20 - 30℃; for 0.5h;
944269-28-7

benzyl(1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-cyclopentane-acetate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;78%

benzyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: benzyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
78%

(1R,2'S,5'R)-methyl(1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-acetate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;77%

(1'R,2'S,5'R)-menthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: (1'R,2'S,5'R)-menthyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
77%

C38H33NO8

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With potassium carbonate In methanol; dichloromethane at 25 - 30℃; Inert atmosphere;77%

ethyl (1R,2R,3R) 3-hydroxy-2-[5-phenyl-(3S)-hydroxy-(1E)-pentenyl]-5-oxo-cyclopentane acetate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -70℃; for 2h; Product distribution / selectivity;75%

ethyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate

41639-74-1

(3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one

Conditions
ConditionsYield
Stage #1: ethyl (1R,2R,3R)-3-hydroxy-2-[5-phenyl-(3S)-3-hydroxy-1-pentenyl]-5-oxo-cyclopentaneacetate With L-Selectride In tetrahydrofuran at -70℃; for 2h; Cooling with methanol-dry ice;
Stage #2: With water; ammonium chloride In tetrahydrofuran Product distribution / selectivity;
75%
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130209-82-4
145667-75-0
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