352276-28-9

Usage

Uses

Used in Pharmaceutical Industry:
Latanoprost Lactol is used as an intermediate in the synthesis of Latanoprost, an F-series prostaglandin analog, for the treatment of glaucoma and various degenerative eye diseases. It helps in reducing intraocular pressure, which is a primary risk factor for glaucoma, and supports the development of effective pharmaceuticals to manage and prevent vision loss associated with these conditions.
Used in Ophthalmology:
In the field of ophthalmology, Latanoprost Lactol is used as a key component in the development of medications that address glaucoma and other eye diseases. Its role in the synthesis of Latanoprost-related analogues contributes to the creation of innovative treatments that can help preserve vision and improve the quality of life for patients suffering from these conditions.
Used in Research and Development:
Latanoprost Lactol is also utilized in research and development for the discovery and design of new pharmaceutical compounds with potential applications in the treatment of glaucoma and other eye diseases. Its unique chemical properties make it a valuable tool for scientists and researchers working to understand the mechanisms of these conditions and develop novel therapeutic strategies.

InChI:InChI=1/C26H40O5.C13H12O3/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;1-9(14)13(15)16-12-7-6-10-4-2-3-5-11(10)8-12/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3;2-9,14H,1H3/b8-3-;/t21-,22+,23+,24-,25+;/m0./s1

Upstream product

• 6742-53-6 (E)-ethyl 4-oxo-2-pentenoate 
• 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 
• 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 
• 37904-38-4 (3S)-5-phenyl-1-penten-3-ol 
• 876953-73-0 tert-butyl[(1S)-3-iodo-1-phenethylpropyl]oxydimethylsilane 
• 474944-31-5 (3S)-3-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-5-phenylpentan-1-ol 
• 160805-51-6 5-phenyl-3<(tert-butyldimethylsilyl)oxy>-pentene 
• 913258-22-7 (S)-1,2-epoxy-4-phenylbutane 
• 1126-76-7 1,2-Epoxy-4-phenylbutane 
• 768-56-9 4-Phenylbut-1-ene 

Downstream Products

• 130209-82-4 latanoprost 
• 41639-83-2 latanoprost acid 
• 145773-22-4 isopropyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(S)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate 
• 41639-84-3 (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF_2α 

Relevant academic research and scientific papers

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.

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

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).

Process for the synthesis of prostaglandins and intermediates thereof

A process is disclosed for the preparation of prostaglandins of the PGF2α-series, in particular Latanoprost, Bimatoprost and Travoprost, which are active in the treatment of ocular hypertensive conditions and glaucoma. The invention also relates to novel intermediates involved in the synthesis of these prostaglandin-PGF2α derivatives.

Process for the synthesis of prostaglandin derivatives

An alternative method for the synthesis of prostaglandin F analogues, in particular, analogues of PGF2α and specifically for the synthesis of latano-prost, wherein the transformation of the lactone intermediate (5) into the corresponding lactol (7) is carried out by treating the lactone intermediate (5) with a silane, preferably polymethylhydrosiloxane (PMHS), in the presence of a titanocene - and preferably titanocene fluoride. The method enables considerable production economies with respect to the conventional reduction of lactone with diisobutylaluminum hydride (DIBAL-H).

Ligand-controlled palladium-catalyzed intramolecular reactions of phenyl-substituted prostaglandin P(2α) analogues

Palladium catalyzed intramolecular cyclization of the 15R and 15S epimers of 17-(2-iodophenyl)-18,19,20-trinorprostaglandin F(2α) isopropylester [(15R)-5 and (15S)-5, respectively] produce a complex mixture of products including various tetrahydronaphthol

Phenyl-Substituted Prostaglandins: Potent and Selective Antiglaucoma Agents

A series of phenyl-substituted analoques of prostaglandin F2α (PGF2α) were prepared and evaluated for ocular hypotensive effect and side effects in different animal models.In addition, the activity of the analogues on FP receptors was studied in vitro.The results were compared with those of PGF2α and its isopropyl ester.The phenyl-substituted PGF2α analogues exhibited good intraocular pressure reducing effect, were more selective, and exhibited a much higher therapeutic index in the eye than PGF2α or its isopropyl ester.The analogues exhibited high activity on FP receptors in a stereoselective manner for the 15a-hydroxyl group.