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Merck
CN

249262

(−)-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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24854983
MDL number:
MFCD00078077
Beilstein/REAXYS Number:
1294692
Assay:
99%
Form:
solid

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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 string

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

InChI key

SZJVIFMPKWMGSX-AKHDSKFASA-N

assay

99%

form

solid

optical activity

[α]20/D −87°, c = 1 in chloroform

functional group

ester, hydroxyl, phenyl

storage temp.

2-8°C

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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)
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.
Aldrichimica Acta, 15, 65-65 (1982)

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