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

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

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 
• 41639-83-2 latanoprost acid 
• 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 
• 67-63-0 isopropyl alcohol 
• 141074-06-8 C₂₆H₃₈O₅ 
• 1513876-38-4 (3aR,6aS)-2-oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde 
• 122-97-4 3-Phenyl-1-propanol 
• 60340-28-5 (S)-1-phenyl-5-hexen-3-ol 
• 1379822-84-0 (-)-(S)-1-phenyl-3-(tert-butyldimethylsilyloxy)-hex-5-ene 

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.

NOVEL LATANOPROST INTERMEDIATE AND METHOD FOR PREPARING LATANOPROST WITH HIGH PURITY

The present invention provides a novel latanoprost intermediate represented by chemical formula 1. In chemical formula 1, R is hydrogen or C_1-C_4 alkyl, P is hydrogen or a hydroxy protecting group, at least one P is a hydroxy protecting group. The hydroxy protecting group is represented by chemical formula 2. In chemical formula 2, R^1 is each independently -NO_2 or C_6-C_18 aryl, and R^1 is fused to a phenyl ring to form a C_10-C_18 aromatic ring.COPYRIGHT KIPO 2021

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.

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.

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.

High-purity Latanoprost, preparation method therefor and use of Latanoprost

The invention discloses high-purity Latanoprost, a preparation method therefor and use of the Latanoprost. According to the high-purity Latanoprost disclosed by the invention, the content of an impurity with a structure represented by a formula II shown in the description in the high-purity Latanoprost is not higher than 0.1%. The preparation method comprises the steps: (1) subjecting a compound represented by a formula IV shown in the description (an intermediate 1 of the Latanoprost) to a wittig reaction, so as to obtain a compound represented by a formula V shown in the description (an intermediate 2 of the Latanoprost); (2) subjecting the compound V to washing and purifying by a ammonium chloride solution, then, carrying out dehydroxylation protection or not, and carrying out a reaction with iodo-isopropane, so as to obtain a crude raw pharmaceutical material of the Latanoprost; and (3) loading a sample of the raw pharmaceutical material of the Latanoprost to a silica-gel column, carrying out eluting with an eluate, and carrying out chromatographic purification, thereby obtaining the high-purity Latanoprost.

Processes for the preparation of isomer free prostaglandins

Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS

Novel processes for the preparation of a compound of Formula I-2 substantially free of the 5,6-trans isomer: wherein R2, R3 and R4 are as defined in the specification are provided. Novel intermediates for the preparations of isomer free Prostaglandins and derivatives thereof are also provided.

A Facile and Efficient Synthesis of (15R)-Latanoprost from Chiral Precursor Corey Lactone Diol

An efficient asymmetric synthetic route for the synthesis of anti-glaucoma agent, (15R)-latanoprost using Corey lactone diol as chiral substrate under Swern oxidation, allylic reduction and Wittig reaction conditions has been developed. In this method, reduction of keto and alkene functional groups has been achieved in a single step using low cost catalyst NiCl2/NaBH4 in methanol. This new synthetic protocol is a good alternative for the synthesis of latanoprost with high stereo selectivity and improved yield. [Figure not available: see fulltext.]

Compound And Method

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is