913258-34-1

Basic information

• Product Name: trans Latanoprost
• Synonyms: (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester;(5E)-Latanoprost;5,6-trans-Latanoprost;trans Latanoprost;5,6-trans-Latanoprost (50.0 Mg in 5.0 Ml Methyl acetate);Latanoprost Related CoMpound A;Latanoprost Related Compound A (50 mg) (Isopropyl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate);5,6-trans-latanprost
• CAS NO: 913258-34-1
• Molecular Formula: C26H40O5
• Molecular Weight: 432.5928
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Aromatics;Chiral Reagents
• Mol File: 913258-34-1.mol

Chemical Properties

• Boiling Point: 583.8 °C at 760 mmHg
• Flash Point: 188.3 °C
• Appearance: /
• Density: 1.093 g/cm³
• Storage Temp.: -80°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.84±0.70(Predicted)
• Stability: Temperature Sensitive
• CAS DataBase Reference: trans Latanoprost(CAS DataBase Reference)
• NIST Chemistry Reference: trans Latanoprost(913258-34-1)
• EPA Substance Registry System: trans Latanoprost(913258-34-1)

Safety Data

• Hazardous Substances Data: 913258-34-1(Hazardous Substances Data)

Usage

Uses

Used in Ophthalmology:
trans Latanoprost is used as an anti-glaucoma agent for reducing intraocular pressure in various types of glaucoma and ocular hypertension. It functions by increasing the outflow of aqueous humor, thus helping to manage and prevent further damage to the optic nerve.
Used in Urology:
trans Latanoprost is used as a PDE5 inhibitor for treating erectile dysfunction. It enhances the erectile response by increasing blood flow to the penis, allowing for a firmer and more sustained erection when sexually stimulated.

Upstream product

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• 477884-73-4 (3aR,4R,5R,6aS)-hexahydro-5-triethylsilyoxy-4-[5-phenyl-(3R)-3-triethylsilyloxy-pentanyl]-2H-cyclopenta[β]furan-2-one 
• 41639-83-2 latanoprost acid 
• 1224443-39-3 latanoprost L-arginine salt 
• 474944-22-4 (Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate 
• 75-26-3 isopropyl bromide 
• 856240-62-5 (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol 
• 58707-50-9 (3aR,4S,5R,6aS)-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 1395618-63-9 (3aR,4S,5R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-5-{[(tert-butyl)(diphenyl)silyl]oxy}-3,3a,5,5,6,6a-hexahydro-2H-cyclopenta[b]furan-2-one 
• 62939-85-9 (-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one 
• 1395618-89-9 (3aR,4S,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-(trityloxymethyl)hexahydro-2H-cyclopenta [b] furan-2-one 
• 1395619-06-3 (3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-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.

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.

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

NEW PROCESS FOR THE PREPARATION OF HIGH PURITY PROSTAGLANDINS

The subject of the invention is a process for the preparation of high purity prostaglandin acid of the general formula II wherein the bonds marked with dotted lines represent single or double bonds wherein the double bonds may be cis- or trans oriented, Y represents 0 or CH 2, and R3 stands for a phenyl group which is optionally substituted with CF3, wherein the crude prostaglandin acid of the general formula II is purified by normal phase silicagel chromatography.

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2?±, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

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.