15(R)-17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER

Base Information

• Chemical Name: 15(R)-17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER
• CAS No.: 130273-87-9
• Molecular Formula: C26H38 O5
• Molecular Weight: 430.585
• Mol file: 130273-87-9.mol

Synonyms:5-Heptenoicacid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-,1-methylethyl ester, (5Z)- (9CI); 5-Heptenoic acid,7-[3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl]-, 1-methylethylester, [1R-[1a(Z),2b(1E,3R*),3a,5a]]-

Chemical Property of 15(R)-17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER

Chemical Property:

• PSA: 86.99000
• LogP: 3.96240

Purity/Quality:

98% ^*data from raw suppliers

15(R)-17-phenyl trinor Prostaglandin F2α isopropyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 15(R)-17-phenyl trinor Prostaglandin F2α isopropyl ester (15(R)-17-phenyl trinor PGF2α isopropyl ester) is the latanoprost-related isomer containing both a double bond at 13,14 and an inverted (β) hydroxyl group at C-15. Similar to 15(S)-latanoprost, 15(R)-17-phenyl trinor PGF2α isopropyl ester is a potential impurity in most commercial preparations of the latanoprost bulk drug product. The IC50 values for the free acid forms of 15(S)-17-phenyl trinor PGF2α and 15(R)-17-phenyl trinor PGF2α were determined to be 0.71 nM and 30 nM, respectively, in a FP receptor binding assay using the cat iris sphincter muscle. A 3 μg dose of 15(R)-17-phenyl trinor PGF2α caused a 1.9 mmHg reduction of IOP in normotensive cynomolgus monkeys.

Technology Process of 15(R)-17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER

There total 6 articles about 15(R)-17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ISOPROPYL ESTER 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: 28.0%

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-77-7) → 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130273-87-9) + 15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-76-6)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; dichloromethane; for 0.5h;

DOI:10.1021/jm00054a008

Reference yield:

(5Z)-bimatoprost acid (38344-08-0) → 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130273-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / DBU / acetone / 10 h / Ambient temperature

2: 76 percent / DDQ / dioxane / 24 h / Ambient temperature

3: 41 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.5 h

With sodium tetrahydroborate; cerium(III) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; dichloromethane; acetone;

DOI:10.1021/jm00054a008

Reference yield:

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130209-76-6) → 15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester (130273-87-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / DDQ / dioxane / 24 h / Ambient temperature

2: 41 percent / NaBH₄, CeCl₃*7H₂O / CH₂Cl₂; methanol / 0.5 h

With sodium tetrahydroborate; cerium(III) chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; dichloromethane;

DOI:10.1021/jm00054a008

upstream raw materials:

15-keto-17-phenyl-18,19,20-trinorprostaglandin F_2α isopropyl ester

dimethyl(2-oxo-4-phenylbutyl)phosphonate

(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester

(5Z)-bimatoprost acid

Downstream raw materials:

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((R)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester