propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

Base Information

• Chemical Name: propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• CAS No.: 913258-34-1
• Molecular Formula: C₂₆H₄₀O₅
• Molecular Weight: 432.601
• Hs Code.: 2937500000
• European Community (EC) Number: 682-020-5
• UNII: ZC39I2T1VW
• Pharos Ligand ID: 2131SFHZWDNP
• ChEMBL ID: CHEMBL364375
• Mol file: 913258-34-1.mol

Synonyms:913258-34-1;trans-Latanoprost;5,6-trans-Latanoprost;Isopropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate;Latanoprost, (5E)-;C26H40O5;ZC39I2T1VW;CHEMBL364375;propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate;Latanoprost [USAN:INN:BAN];XA 41;5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester, (5E)-;Isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate;5-trans-Latanoprost;Latanoprost [USAN:BAN:INN];C26-H40-O5;5-trans Latanoprost;starbld0017089;PhXA34;UNII-ZC39I2T1VW;LATANOPROST (PHXA41);SCHEMBL1286379;SCHEMBL1649402;CHEBI:94503;5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester, (1R-(1-alpha(Z),2-beta(R*),3-alpha,5-alpha))-;AMY30126;BDBM50150899;PDSP2_001702;AKOS016002154;LS-74633;LATANOPROST IMPURITY F [EP IMPURITY];J-502634;13,14-dihydro-15(R)-17-phenyl-18,19,20-trinor-prostaglandin-2-alpha-isopropyl ester;(E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((R)-3-hydroxy-5-phenyl-pentyl)-cyclopentyl]-hept-5-enoic acid isopropyl ester;(Z)-isopropyl 7-((1R,2R)-3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate;5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-,1-methylethyl ester, (1R-(1-alpha(Z),2-beta(R*),3-alpha,5-alpha))-;5-Heptenoicacid,7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-,1-methylethyl ester,(5E)-

Chemical Property of propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

Chemical Property:

• Boiling Point: 583.8 °C at 760 mmHg
• PKA: 14.84±0.70(Predicted)
• Flash Point: 188.3 °C
• PSA: 86.99000
• Density: 1.093 g/cm³
• LogP: 4.18640
• Storage Temp.: -80°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 14
• Exact Mass: 432.28757437
• Heavy Atom Count: 31
• Complexity: 526

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-Latanoprost ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)OC(=O)CCCC=CCC1C(CC(C1CCC(CCC2=CC=CC=C2)O)O)O
• Isomeric SMILES: CC(C)OC(=O)CCC/C=C/C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
• Uses: trans Latanoprost is a PDE5 inhibitor for erectile dysfunction. Prostaglandin analog; prodrug of active acid metabolite. It is a synthetic derivative of the natural prostaglandin PGF2α, used as an anti-glaucoma agent that is effective in various types of glaucoma and ocular hypertension. Latanoprost USP Related Compound A. Prostaglandin analog; prodrug of active acid metabolite. It is a synthetic derivative of the natural prostaglandin PGF2α, used as an anti-glaucoma agent that is effective in various types of glaucoma and ocular hypertension.

Technology Process of propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

There total 161 articles about propan-2-yl (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.83%

2-iodo-propane (75-30-9) + latanoprost acid (41639-83-2) → isopropyl (E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate (145773-22-4,913258-34-1) + latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃; for 14h;

DOI:10.1002/ejoc.200600749

Reference yield: 99.83%

2-iodo-propane (75-30-9) + latanoprost acid (41639-83-2) → isopropyl (E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate (145773-22-4,913258-34-1) + latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetone; at 20 ℃; for 14h;

DOI:10.1002/ejoc.200600749

Reference yield: 92.0%

latanoprost acid (41639-83-2) + isopropyl alcohol (67-63-0,8013-70-5) → latanoprost (130209-82-4,145773-22-4,913258-34-1)

Guidance literature:

With Lipase Novozym 435; at 30 ℃; for 18h; Enzymatic reaction;

upstream raw materials:

2-iodo-propane

(15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF_2α

(-)-Corey lactone 5-(4-phenylbenzoate)

benzyl bromide

Refernces

• 1、 -. "NOVEL LATANOPROST INTERMEDIATE AND METHOD FOR PREPARING LATANOPROST WITH HIGH PURITY". Paragraph 0066; 0076-0078. . Retrieved 2020/10/21.
• 2、 Sasane, Sachin A.,Bhise, Nandu B.,Singh, Girij P.,Joseph, Alex,Shenoy, Gautham G.. "An improved synthesis of latanoprost involving effective control on 15(S) diastereomer". . p. 2350 - 2356. Retrieved 2019/07/31.