| Identification | More | [Name]
(3aR,4S,5R,6aS)-(-)-5-(Benzoyloxy)-hexahydro-4(-hydroxymethyl)-2H-cyclopenta[b]furan-2-one | [CAS]
39746-00-4 | [Synonyms]
(3AR,4S,5R,6AS)-(-)-5-(BENZOYLOXY)-HEXAHYDRO-4(-HYDROXYMETHYL)-2H-CYCLOPENTA[B]FURAN-2-ONE
5-(BENZOYLOXY) HEXAHYDRO-4-(HYDROXYMETHYL)-2H-CYCLOPENTA[B]FURAN-2-ONE (3AA,4A,5BETA,6AA)
(-)-6-BETA-HYDROXYMETHYL-7-ALPHA-BENZOYLOXY-CIS-2-OXABICYCLO[3.3.0]OCTAN-3-ONE
(-)-COREY LACTONE BENZOATE
COREY'S LACTONE
(-)-5-(benzoyloxy)hexahydro-4-(hydroxyme)-2H-cycl
[3aR-(3aalpha,4alpha,5beta,6aalpha)]-hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate
5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one(3aα,4α,5β,6aα)
(-)-5-(BENZOYLOXY)HEXAHYDRO-4-(HYDROXYME)-2H-CYCLOPENTA(B)FURAN-2-ONE, 97%
5-(BENZOYLOXY) HEXAHYDRO-4-(HYDROXYMETHYL)-2H-CYCLOPENTA[B]FURAN-2-ONE
BENZOYL COREY LACTONE
(-)-COREY LACTONE BENZOATE 99%
(-)-Corey lactone benzoate
(-)-COREY LACTONE BENZOATE: (3AR,4S,5R,6AS)-(-)-5-(BENZOYLOXY)-HEXAHYDRO-4(-HYDROXYMETHYL)-2H-CYCLOPENTA[B]FURAN-2-ONE
(-)-6-BETA-HYDROXYMETHYL-7-ALPHA-BENZOYLOXY-CIS-2-OXABICYCLO[3.3.0]OCTAN-3-ONE(COREY''S LACTONE)
(1R)-2β-(Hydroxymethyl)-3α-(benzoyloxy)-5α-hydroxycyclopentane-1α-acetic acid 1,5-lactone
(1S,5R,6S,7R)-7-Benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one
(3aβ,6aβ)-4β-(Hydroxymethyl)-5α-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one | [EINECS(EC#)]
254-615-6 | [Molecular Formula]
C15H16O5 | [MDL Number]
MFCD00674102 | [Molecular Weight]
276.28 | [MOL File]
39746-00-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless crystalline powder | [Melting point ]
116-120 °C
| [alpha ]
-80 º (c=0.8, CHCl3 25 ºC) | [Boiling point ]
379.19°C (rough estimate) | [density ]
1.2379 (rough estimate) | [refractive index ]
1.5000 (estimate) | [storage temp. ]
-20°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
14.79±0.10(Predicted) | [color ]
White to Pale Yellow | [InChI]
InChI=1S/C15H16O5/c16-8-11-10-6-14(17)19-12(10)7-13(11)20-15(18)9-4-2-1-3-5-9/h1-5,10-13,16H,6-8H2/t10-,11-,12+,13-/m1/s1 | [InChIKey]
OBRRYUZUDKVCOO-FVCCEPFGSA-N | [SMILES]
O1C(=O)C[C@]2([H])[C@@H](CO)[C@H](OC(=O)C3=CC=CC=C3)C[C@]12[H] | [CAS DataBase Reference]
39746-00-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [HS Code ]
29321900 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless crystalline powder | [Uses]
(-)-Corey Lactone Benzoate is a corey lactone derivative used in the preparation prostaglandin analogues for use as vasolidator as well as EP4 receptor agonists. | [Synthesis]
A 1:1 methanol:methylene chloride solution (40 mL) of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carbaldehyde (1) (purchased from Cayman Chemical Company, Ann Arbor, MI) (3.5 g, 12.8 mmol) in a 1:1 methanol:dichloromethane solution (40 mL). After 25 min of reaction, the reaction was quenched by careful addition of saturated aqueous citric acid solution (60 mL). The mixture was extracted with ethyl acetate (3 × 40 mL) and the organic layers were combined and washed sequentially with water (2 × 80 mL) and saturated saline (2 × 80 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the target compound 2 (2.43 g, 69% yield). | [References]
[1] Patent: US6353000, 2002, B1. Location in patent: Page column 10
[2] Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 290, # 3, p. 1278 - 1284
[3] Patent: US6353014, 2002, B1. Location in patent: Page column 18 |
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