Methyl (3E,5Z,11alpha,13E,16R)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprosta-3,5,13-trien-1-oate

Base Information

• Chemical Name: Methyl (3E,5Z,11alpha,13E,16R)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprosta-3,5,13-trien-1-oate
• CAS No.: 81834-84-6
• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.509
• Mol file: 81834-84-6.mol

Synonyms:15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester;15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester, 16S-(+-)-isomer;15-DMHDPE2

Chemical Property of Methyl (3E,5Z,11alpha,13E,16R)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprosta-3,5,13-trien-1-oate

Chemical Property:

• Vapor Pressure: 1.56E-12mmHg at 25°C
• Boiling Point: 509.9°Cat760mmHg
• Flash Point: 167.4°C
• Density: 1.106g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 378.24062418
• Heavy Atom Count: 27
• Complexity: 563

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC(C)(CC=CC1C(CC(=O)C1CC=CC=CCC(=O)OC)O)O
• Isomeric SMILES: CCCC[C@](C)(C/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\C=C\CC(=O)OC)O)O

Technology Process of Methyl (3E,5Z,11alpha,13E,16R)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprosta-3,5,13-trien-1-oate

There total 10 articles about Methyl (3E,5Z,11alpha,13E,16R)-(+-)-11,16-dihydroxy-16-methyl-9-oxoprosta-3,5,13-trien-1-oate 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: 44.0%

(+/-)-methyl 11α,16-dihydroxy-16-methyl-9-oxoprosta-3(E),13(E)-dien-5-yn-1-oate (105430-91-9,105430-92-0,112137-97-0) → (+/-)-15-deoxy-16-methyl-16-hydroxy-3(E)-didehydroprostaglandin E2 methyl ester (81834-82-4,81834-83-5,81834-84-6,81834-85-7,81834-90-4,81834-91-5,81834-92-6,81834-93-7,81834-96-0,81834-97-1,81873-58-7,81873-59-8,112137-92-5,112137-93-6,112244-30-1,119239-56-4)

Guidance literature:

With sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine; In ethanol; for 0.666667h;

DOI:10.1021/jm00384a032

Reference yield:

methyl 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-5(Z)-heptenoate (54594-85-3) → (+/-)-15-deoxy-16-methyl-16-hydroxy-3(E)-didehydroprostaglandin E2 methyl ester (81834-82-4,81834-83-5,81834-84-6,81834-85-7,81834-90-4,81834-91-5,81834-92-6,81834-93-7,81834-96-0,81834-97-1,81873-58-7,81873-59-8,112137-92-5,112137-93-6,112244-30-1,119239-56-4)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 1 h / Ambient temperature

2: 2.) hexamethylphosphoric triamide (HMPT) / 1.) ether, -60 deg C, 1 h, 2.) ether, -20 deg C, 1 h

3: 90 percent / N-isopropylcyclohexylamine,n-BuLi / tetrahydrofuran / -60 °C

4: 40 percent / 30percent H₂O₂, pyridine / CH₂Cl₂; H₂O / 4 h / Ambient temperature

5: N-isopropylcyclohexylamine, N-BuLi, hexamethylphosphoric triamide (HMPT) / tetrahydrofuran

6: AcOH / tetrahydrofuran; H₂O / 24 h / Ambient temperature

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; dihydrogen peroxide; acetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00157a013

Reference yield:

(+/-)-methyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-16-methyl-2-(phenylseleno)-11α-<(triethylsilyl)oxy>-16-<(trimethylsilyl)oxy>prosta-5(Z),8,13(E)-trien-1-oate → (+/-)-15-deoxy-16-methyl-16-hydroxy-3(E)-didehydroprostaglandin E2 methyl ester (81834-82-4,81834-83-5,81834-84-6,81834-85-7,81834-90-4,81834-91-5,81834-92-6,81834-93-7,81834-96-0,81834-97-1,81873-58-7,81873-59-8,112137-92-5,112137-93-6,112244-30-1,119239-56-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / 30percent H₂O₂, pyridine / CH₂Cl₂; H₂O / 4 h / Ambient temperature

2: N-isopropylcyclohexylamine, N-BuLi, hexamethylphosphoric triamide (HMPT) / tetrahydrofuran

3: AcOH / tetrahydrofuran; H₂O / 24 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; dihydrogen peroxide; acetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jm00157a013

upstream raw materials:

(+/-)-methyl 11α,16-dihydroxy-16-methyl-9-oxoprosta-3(E),13(E)-dien-5-yn-1-oate

methyl 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-5(Z)-heptenoate

(+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-5(Z)-heptenoate

methyl 3-butynoate

Refernces

• 1、 Collins, Paul W.,Gasiecki, Alan F.,Jones, Peter H.,Bauer, Raymond F.,Gullikson, Gary W.,et al.. "Synthesis and Gastric Antisecretory Properties of α Chain Diene Derivatives of Misoprostol". . p. 1195 - 1201. Retrieved 2007/10/02.