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

• ChemBase ID: 126709
• Molecular Formular: C21H20O5
• Molecular Mass: 352.3805
• Monoisotopic Mass: 352.13107374
• SMILES: OC[C@H]1[C@@H](C[C@@H]2OC(=O)C[C@H]12)OC(=O)c1ccc(cc1)c1ccccc1
• Canonical SMILES: OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)OC(=O)c1ccc(cc1)c1ccccc1
• 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
• InChIKey: SZJVIFMPKWMGSX-AKHDSKFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,4S,5R,6aS)-4-(hydroxymethyl)-2-oxo-hexahydro-2H-cyclopenta[b]furan-5-yl 4-phenylbenzoate
• IUPAC Traditional name: corey lactone 4-phenylbenzoate
• Synonyms: (3aα,4α,5β,6aα)-(-)-Hexahydro-4-(hydroxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl 1,1′-biphenyl-4-carboxylate; (3aR,4S,5R,6aS)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzoyloxy)cyclopenta[b]furan-2-one; (-)-Corey lactone, 4-phenylbenzoate alcohol; Corey lactone 4-phenylbenzoate; (3aR,4S,5R,6aS)-Hexahydro-4-(hydroxymethyl)-5-(4-phenylbenzoyloxy)cyclopenta[b]furan-2-one; (-)-Corey Lactone 4-Phenylbenzoate Alcohol; Corey Lactone; (-)-Corey Lactone 5-(4-Phenylbenzoate); (3aα,4α,5β,6aα)-(-)-六氢-4-(羟甲基)-2-氧代-2H-环戊并[b]呋喃-5-基1,1′-联苯-4-甲酸酯; (3aR,4S,5R,6aS)-六氢-4-羟甲基-5-(4-苯基苯甲酰氧基)环戊并[b]呋喃-2-酮; (-)-科里内酯4-苯基苯甲酸醇

Database IDs

• CAS Number: 31752-99-5
• MDL Number: MFCD00078077
• Beilstein Number: 1294692
• PubChem SID: 162221037; 24854983
• PubChem CID: 2724295
• Wikipedia Title: Corey_lactone_4-phenylbenzoate

CALCULATED PROPERTIES

• Acid pKa: 15.374329
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.6427593
• LogD (pH = 7.4): 2.6427593
• Log P: 2.6427593
• Molar Refractivity: 94.8059 cm^3
• Polarizability: 38.50716 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 131-132 °C; 131-132 °C(lit.); 133-135°C
• Optical Rotation: [α]20/D -87°, c = 1 in chloroform; [α]20/D -88±1°, c = 1% in chloroform

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 99%
• Grade: purum
• Empirical Formula (Hill Notation): C21H20O5

DETAILS

Sigma Aldrich - 249262

Packaging
1 g in glass bottle
Application
Key intermediate in the synthesis of prostaglandins.1,2 Versatile building block for prostaglandins. Building block for a potent and selective antiglaucoma agent analog of PGF2α2

Sigma Aldrich - 52535

Other Notes
Important intermediate in the synthesis of prostaglandins1,2

Toronto Research Chemicals - C695000

Key intermediate in the synthesis of prostaglandins. Versatile building block for prostaglandins. Building block for a potent and selective antiglaucoma agent analog of PGF2α.

REFERENCES

• Carpio, H., et al.: Prostaglandins, 33, 169 (1987)
• Resul, B., et al.: J. Med. Chem., 36, 243 (1987)