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

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

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

• 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 
• 6742-53-6 (E)-ethyl 4-oxo-2-pentenoate 
• 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 
• 62961-72-2 Corey aldehyde 
• 542-92-7 cyclopenta-1,3-diene 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 353522-93-7 (3aR,4R,5R,6aS)-4-((R)-3-hydroxy-5-phenylpentyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 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 
• 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 
• 100-39-0 benzyl bromide 

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.

Access to a Key Building Block for the Prostaglandin Family via Stereocontrolled Organocatalytic Baeyer–Villiger Oxidation

A new protocol for the construction of a crucial bicyclic lactone of prostaglandins using a stereocontrolled organocatalytic Baeyer–Villiger (B-V) oxidation was developed. The key B-V oxidation of a racemic cyclobutanone derivative with aqueous hydrogen peroxide has enabled an early-stage construction of a bicyclic lactone skeleton in high enantiomeric excess (up to 95 %). The generated bicyclic lactone is fully primed with two desired stereocenters and enabled the synthesis of the entire family of prostaglandins according to Corey′s route. Furthermore, the reactivity and enantioselectivity of B-V oxidation of racemic bicyclic cyclobutanones were evaluated and 90–99 % ee was obtained, representing one of the most efficient routes to chiral lactones. This study further facilitates the synthesis of prostaglandins and chiral lactone-containing natural products to promote drug discovery.

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

An improved synthesis of latanoprost involving effective control on 15(S) diastereomer

An improved process for the synthesis of latanoprost having excellent optical purity (de 99.9%, [α]D20 = +35.37° (c = 0.90, acetonitrile)) without use of preparative HPLC is described. This process involves effective purification of hydroxyl intermediate (5A) through solvent crystallization followed by inhibition of inversion of the chiral center at C-15 position. This was possible due to judicious use of diol intermediate (6) for double bond reduction prior to hydroxyl protection.

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.

Improved Process for the Production of Prostaglandins and Prostaglandin Analogs

The present invention relates to an improved process for the production of prostaglandins and prostaglandin analogs. In particular, this invention relates to the production of prostaglandins of the PGF2α-series, including latanoprost, travoprost, and bimatoprost, which are active pharmaceutical ingredients used for the reduction of elevated intraocular pressure in patients with glaucoma and ocular hypertension.

IMPROVED PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND ANALOGUES THEREOF

The present invention relates to an improved process for the preparation of prostaglandin and prostaglandin analogues, particularly PGF2α derivatives.

Method for preparing prostaglandin F analogue

A method for preparing a prostaglandin F analogue represented by the following formula (I) is disclosed, wherein R1, and are as defined in the specification.

Method for preparing prostaglandin derivative

A method for preparing a prostaglandin derivative represented by the following general formula (I): (wherein Ph represents phenyl group, R1 represents a C1-7 alkyl group, a C1-7 alkenyl group, phenyl group, or benzyl group), which comprises the successive steps (1) to (8) described in the specification, or any one step or two or more successive steps selected from the group consisting of the steps (1) to (8). A method for efficiently, inexpensively and safely preparing prostaglandin derivatives, of which typical example is latanoprost, is provided.

METHOD FOR PREPARING PROSTAGLANDIN DERIVATIVE

A method for preparing a prostaglandin derivative represented by the following general formula (I): (wherein Ph represents phenyl group, R1 represents a C1-7 alkyl group, a C1-7 alkenyl group, phenyl group, or benzyl group), which comprises the successive steps (1) to (8) described in the specification, or any one step or two or more successive steps selected from the group consisting of the steps (1) to (8). A method for efficiently, inexpensively and safely preparing prostaglandin derivatives, of which typical example is latanoprost, is provided.