145773-22-4

Basic information

• Product Name: 15(S)-Latanoprost
• Synonyms: 15(S)-LATANOPROST;15(S)-LATANOPROST ISOPROPYL ESTER;15-EPI LATANOPROST ISOPROPYL ESTER;9ALPHA,11ALPHA,15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROST-5Z-EN-1-OIC ACID ISOPROPYL ESTER;(5Z,9ALPHA,11ALPHA,15S)-9,11,15-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROST-5Z-EN-1-OATE ISOPROPYL ESTER;(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid isopropyl ester;15-epi Latanoprost;(5Z,9α,11α,15S)-9,11,15-Trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate isopropyl ester
• CAS NO: 145773-22-4
• Molecular Formula: C26H40O5
• Molecular Weight: 432.59
• EINECS: 201-185-2
• Product Categories: Chiral Reagents;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 145773-22-4.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 583.839 °C at 760 mmHg
• Flash Point: -16 °C
• Appearance: /
• Density: 1.094 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: −20°C
• PKA: 14.84±0.70(Predicted)
• CAS DataBase Reference: 15(S)-Latanoprost(CAS DataBase Reference)
• NIST Chemistry Reference: 15(S)-Latanoprost(145773-22-4)
• EPA Substance Registry System: 15(S)-Latanoprost(145773-22-4)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36-66-67
• Safety Statements: 16-26-29-33
• RIDADR: UN 1231 3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 145773-22-4(Hazardous Substances Data)

Usage

Description

15(S)-Latanoprost is an enantiomer of Latanoprost, a synthetic prostaglandin F2α analog, which is primarily used in the pharmaceutical industry. It is known for its ocular hypotensive properties, making it a significant component in glaucoma treatment. As an impurity in commercially prepared Latanoprost, 15(S)-Latanoprost is a relevant compound in the context of quality control and drug development.

Uses

Used in Pharmaceutical Industry:
15(S)-Latanoprost is used as an impurity reference for the quality control and development of Latanoprost (L177280). It is essential in ensuring the purity and efficacy of the final drug product, which is crucial for the treatment of glaucoma and other ocular hypertensive conditions.
Used in Quality Control:
15(S)-Latanoprost is used as a reference compound for the identification and quantification of impurities in commercially prepared Latanoprost. This helps in maintaining the safety and efficacy of the drug, as well as adhering to regulatory standards.
Used in Research and Development:
As an enantiomer of Latanoprost, 15(S)-Latanoprost is used in research and development for studying the stereoselectivity of the drug and its potential effects on the pharmacological activity. This can lead to the optimization of drug formulations and the development of more effective treatments for glaucoma and other related conditions.
Used in Regulatory Compliance:
15(S)-Latanoprost is used as a reference compound in the development and validation of analytical methods for the detection and quantification of impurities in Latanoprost. This ensures that the drug meets the required regulatory standards for quality, safety, and efficacy.

InChI:InChI=1/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22-,23-,24+,25-/m1/s1

Upstream product

• 75-30-9 2-iodo-propane 
• 41639-84-3 (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF_2α 
• 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 
• 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 
• 145667-75-0 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 
• 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 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 41639-83-2 latanoprost acid 
• 477884-73-4 (3aR,4R,5R,6aS)-hexahydro-5-triethylsilyoxy-4-[5-phenyl-(3R)-3-triethylsilyloxy-pentanyl]-2H-cyclopenta[β]furan-2-one 
• 41639-23-0 (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one 
• 145773-21-3 (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one 

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.

Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst

An enantioselective total synthesis of latanoprost was achieved. Its chiral cyclopentane core structure was constructed through an organocatalyst-mediated [3+2]-cycloaddition reaction, and chirality in the ω-side chain was generated by prolinate-anion-mediated α-aminoxylation of an aldehyde. Highly diastereoselective domino acetalization and an oxy-Michael reaction were key steps for the generation of C9 chirality.