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249262

Sigma-Aldrich

(−)-Corey lactone, 4-phenylbenzoate alcohol

99%

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):
C21H20O5
CAS Number:
31752-99-5
Molecular Weight:
352.38
Beilstein:
1294692
MDL number:
MFCD00078077
UNSPSC Code:
12352005
PubChem Substance ID:
24854983
NACRES:
NA.22

Assay

99%

form

solid

optical activity

[α]20/D −87°, c = 1 in chloroform

mp

131-132 °C (lit.)

functional group

ester
hydroxyl
phenyl

storage temp.

2-8°C

SMILES string

OC[C@H]1[C@@H](C[C@@H]2OC(=O)C[C@H]12)OC(=O)c3ccc(cc3)-c4ccccc4

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

InChI key

SZJVIFMPKWMGSX-AKHDSKFASA-N

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General description

(−)-Corey lactone, 4-phenyl benzoate alcohol, also known as 2H-cyclopenta[b]furan, [1,1′-biphenyl]-4-carboxylic acid derivative, is commonly used as a chiral substrate and is a versatile building block for prostaglandins.

Application

(−)-Corey lactone, 4-phenyl benzoate alcohol is used as:
  • A substrate in the synthesis of tricyclic cyclopent[b]benzofuran.
  • A Key intermediate in the synthesis of prostaglandins.
  • Building block for a potent and selective antiglaucoma agent analog of PGF2α

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS9769
MKCS3628
MKCM9094
MKCK7735
MKCK7737

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A practical synthesis of chiral tricyclic cyclopenta [b] benzofuran, a key intermediate of Beraprost
Xiaoyu L,et al.
Organic & Biomolecular Chemistry, 14, 7715-7721 (2016)
Pot and time economies in the total synthesis of Corey lactone
Nariyoshi U,et al.
Chemical Science, 11, 1205-1209 (2020)
Aldrichimica Acta, 15, 65-65 (1982)
B Resul et al.
Journal of medicinal chemistry, 36(2), 243-248 (1993-01-22)
A series of phenyl-substituted analogues of prostaglandin F2 alpha (PGF2 alpha) were prepared and evaluated for ocular hypotensive effect and side effects in different animal models. In addition, the activity of the analogues on FP receptors was studied in vitro.

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