(-)-Corey lactone 4-phenylbenzoate alcohol

CAS No:
31752-99-5

Molecular Formula：

C21H20O5

Molecular Weight：

352.38

Storage:

Store in a tightly closed container in a cool, dry，Protect from moisture and direct sunlight.

Synonyms:

(-)-Corey lactone 4-phenylbenzoate
(-)-Corey lactone 4-phenylbenzoate alcohol
(3aR,4S,5R,6aS)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzoyloxy)cyclopenta[b]furan-2-one
MFCD00078077
253659726

IUPAC Name:

[(3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] 4-phenylbenzoate

InChIKey:

SZJVIFMPKWMGSX-AKHDSKFASA-N

InChI:

InChI=1S/C21H20O5/c22-12-17-16-10-20(23)25-18(16)11-19(17)26-21(24)15-8-6-14(7-9-15)13-4-2-1-3-5-13/h1-9,16-19,22H,10-12H2/t16-,17-,18+,19-/m1/s1

SMILES:

C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)CO

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Technical Data

Appearance	White to almost white powder
Solubility	Soluble in chloroform,ethyl acetate,acetone,Practically insoluble in water
Specific rotation(alpha)	-89° to -83°(20℃,C=1,CHCI3)
Melting Point	129℃ to 134℃
Loss on drying	≤1.0%
E.E value	≥99.9%
Assay	98%-102%

Description

Key intermediate for prostaglandin synthesis: It is the chiral intermediate for the synthesis of the prostaglandin PGF2α drug.

Safety Information

GHS

Pictogram:

GHS07

Signal Word:

Warning

Hazard Statements:

H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.

Precautionary Statements:

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes.
Remove contact lenses, if present and easy to do. Continue rinsing.

References

1.Synthesis and gastric antisecretory properties of allenic 16-phenoxy-omega-tetranor prostaglandin E analogs. | Carpio, H., et al. 1987. Prostaglandins. 33: 169-80. PMID: 3588969
2.Phenyl-substituted prostaglandins: potent and selective antiglaucoma agents. | Resul, B., et al. 1993. J Med Chem. 36: 243-8. PMID: 8423596

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