145667-75-0

Basic information

• Product Name: Latanoprost Lactone Diol
• Synonyms: LATANOPROST LACTONE DIOL;(3AR,4R,5R,6AS)-HEXAHYDRO-5-HYDROXY-4-[(3R)-3-HYDROXY-5-PHENYLPENTYL]-2H-CYCLOPENTA[B]FURAN-2-ONE;(3AR,4R,5R,6AS)-5-HYDROXY-4-((3R)-3-HYDROXY-5-PHENYLPENTYL)HEXAHYDROCYCLOPENTA[B]FURAN-2-ONE;LP-diol (LT-DI)(Latanprost);LP-diol;2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]-, (3aR,4R,5R,6aS)-;(3AR,4R,5R,6aS)-5-Hydroxy-4-((R)-3-hydroxy-5-phenyl-pentyl)hexahydro-2H-cyclopenta[b]furan-2-one;(3AR,4R,5R,6aS)-5-Hydroxy-4-((R)-3-hydroxy-5-phenyl-pentyl)hexahydro-2H-cyclopenta[b]furan-2-o
• CAS NO: 145667-75-0
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.38
• Mol File: 145667-75-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 69-71 ºC
• Boiling Point: 522.959 °C at 760 mmHg
• Flash Point: 190.276 °C
• Appearance: White or almost white crystalline powder
• Density: 1.202
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.58±0.40(Predicted)
• CAS DataBase Reference: Latanoprost Lactone Diol(CAS DataBase Reference)
• NIST Chemistry Reference: Latanoprost Lactone Diol(145667-75-0)
• EPA Substance Registry System: Latanoprost Lactone Diol(145667-75-0)

Safety Data

• Hazardous Substances Data: 145667-75-0(Hazardous Substances Data)

Usage

Description

Latanoprost Lactone Diol, also known as (3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]2H-cyclopenta[b]furan-2-one, is a phenyl-substituted prostaglandin derived from hydrolyzable tannins. It possesses potent and selective properties as an antiglaucoma agent, making it a promising pharmaceutical candidate for various applications.

Uses

Used in Pharmaceutical Industry:
Latanoprost Lactone Diol is used as an antiglaucoma agent for its potent and selective properties in treating glaucoma. It helps in reducing intraocular pressure, which is a primary risk factor for glaucoma progression.
Used in Ophthalmology:
In the field of ophthalmology, Latanoprost Lactone Diol is used as a therapeutic agent for managing glaucoma and other related eye conditions. Its effectiveness in reducing intraocular pressure makes it a valuable asset in preventing vision loss and preserving the quality of life for patients with glaucoma.
Used in Drug Development:
Latanoprost Lactone Diol is also utilized in the development of new drugs and therapies for glaucoma and other eye-related disorders. Its unique properties as a phenyl-substituted prostaglandin make it a valuable compound for researchers to study and potentially develop more effective treatments for glaucoma and other eye conditions.

InChI:InChI=1/C18H24O4/c19-13(7-6-12-4-2-1-3-5-12)8-9-14-15-10-18(21)22-17(15)11-16(14)20/h1-5,13-17,19-20H,6-11H2/t13-,14+,15+,16+,17-/m0/s1

Upstream product

• 145667-74-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 100-39-0 benzyl bromide 
• 41639-72-9 (1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 41639-73-0 (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 353522-93-7 (3aR,4R,5R,6aS)-4-((R)-3-hydroxy-5-phenylpentyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 41639-74-1 (3aR,4R,5R,6aS)-hexahydro-5-hydroxy-4-[(1E,3S)-5-phenyl-3-hydroxy-(1E)-pentenyl]-2H-cyclopentane [β] furan-2-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 542-92-7 cyclopenta-1,3-diene 
• 62961-72-2 Corey aldehyde 
• 933789-26-5 (3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-oxo-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 6742-53-6 (E)-ethyl 4-oxo-2-pentenoate 

Downstream Products

• 352276-28-9 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol 
• 41639-84-3 (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF_2α 
• 145773-22-4 isopropyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(S)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate 
• 61263-22-7 (3aR,4R,5R,6aS)-4-((3R)-5-phenyl-3-((tetrahydro-2H-pyran-2-yl)oxy)pentyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one 
• 477884-73-4 (3aR,4R,5R,6aS)-hexahydro-5-triethylsilyoxy-4-[5-phenyl-(3R)-3-triethylsilyloxy-pentanyl]-2H-cyclopenta[β]furan-2-one 
• 147921-11-7 C₁₈H₂₆O₄ 
• 147921-12-8 C₁₈H₂₆O₄ 
• 1240483-21-9 (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 856453-29-7 (3aR,4R,5R,6aS)-4-((3R)-5-phenyl-3-((tetrahydro-2H-pyran-2-yl)oxy)pentyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-ol 
• 41639-83-2 latanoprost acid 
• 130209-82-4 latanoprost 

Relevant articles and documents

Asymmetric Synthesis of Corey Lactone and Latanoprost

Corey lactone was synthesized in a single pot within 152 minutes in a 50 % overall yield via pot and time economical manner. Latanoprost, an antiglaucoma blockbuster drug, was also synthesized via seven pot reaction with five purifications in a 25 % total yield. One of the key reactions is asymmetric domino Michael/Michael reaction, formal [3+2] cycloaddition reaction, of 3-(dimethylphenylsilyl)propenal and ethyl 4-oxo-2-pentenoate, catalyzed by diphenylprolinol silyl ether, which constructed the core substituted cyclopentanone derivative with nearly optically pure form.

Secondary compounds in the catalytic hydrogenation of enone and allylic alcohol prostaglandin intermediates: Isolation, characterization, and X-ray crystallography

The discovery of the intraocular pressure reduction of 13,14-hydrogenated prostaglandins, among which Latanoprost is the most used drug in glaucoma treatment, has stimulated researchers to improve the synthesis of prostaglandins and their structural analo

PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF PROSTAGLANDINS

A method for preparing cyclopentanones or lactones is provided to be useful for preparation of prostagladins, to remove problems such as the long synthesis route and the removal of undesired isomers, and thus achieves a simple and economical synthesis route. The method for preparing a compound of the following formula II having an enantiomer purity higher than 95% e.e.(enantiomeric excess) comprises the steps of: reacting a compound of the following formula IV having an optical purity higher than 90% e.e. with cuprate; and optionally performing a de-protection reaction of the obtained compound to convert P1, P2, or both P1 and P2 into H. In the formulae, Z does not take part in coupling and de-protection reactions and is an optional group acting as a leaving group in reduction/lactonization reactions, R2 is a single bond, C1-4 alkylene or -CH2O- group, R3 is a C1-7-alkyl or aryl or aralkyl unsubstituted or substituted by C1-4 alkyl, halogen or trihalomethyl, X1 and X2 are independently hydrogen or P1 and P2, respectively, wherein P1 and P2 are protective groups for hydroxyl groups which are identical to or different from each other.