(8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester

Base Information

• Chemical Name: (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester
• CAS No.: 76817-55-5
• Molecular Formula: C₂₃H₄₀O₆
• Molecular Weight: 412.567
• Mol file: 76817-55-5.mol

Synonyms:

Chemical Property of (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester

There total 18 articles about (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl 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: 8.0%

(8R,11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prost-13-dien-1-oic acid methyl ester (125151-77-1) → mexiprostil (76822-56-5,88980-20-5) + (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester (76817-55-5,88980-20-5)

Guidance literature:

With acetic acid; In tetrahydrofuran; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88229-6

Reference yield:

7-[(1R,2R,3R)-2-[(E)-(3S,4S)-4-Methoxy-4-methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-5-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester (76817-53-3) → (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester (76817-55-5,88980-20-5)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 45 ℃; for 2h;

DOI:10.1021/jm00160a005

Reference yield:

n-hexan-2-one (591-78-6) → (8R,11R,12R,15S,16S)-11,15-diydroxy-16-methyl-16-methoxy-9-oxo-prost-13-en-1-oic acid methyl ester (76817-55-5,88980-20-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / Na₂S₂O₅ / H₂O / a) below 40 deg C, 30 min, b) 0 deg C, 2 h

2: 68 percent / HCl(g) / 0 - 5 °C

3: 1.) NaH / 1.) THF, 2.) THF, reflux, 30 min

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 2 h

5: 1.) NaH / 1.) DME, 1 h, 2.) DME, 5 h

6: 58.6 percent / NaBH₄ / methanol; H₂O / 2 h / -78 °C

7: p-toluenesulfonic acid / benzene / 0.5 h / Ambient temperature

8: K₂CO₃ / methanol / 24 h / Ambient temperature

9: pyr2*CrO₃ (Collins reagent) / CH₂Cl₂ / 1 h

10: H₂O, CH₃COOH / tetrahydrofuran / 2 h / 45 °C

With hydrogenchloride; sodium metabisulfite; sodium tetrahydroborate; n-butyllithium; water; dipyridine chromium trioxide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water; benzene;

DOI:10.1021/jm00160a005

upstream raw materials:

(8R,11R,12R,15R,16R)-11,15-di-t-butyldimethylsiloxy-7-hydroxy-16-methyl-16-methoxy-9-oxo-prost-13-dien-1-oic acid methyl ester

7-[(1R,2R,3R)-2-[(E)-(3S,4S)-4-Methoxy-4-methyl-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-5-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-heptanoic acid methyl ester

n-hexan-2-one

(+/-)-2-methyl-2-hydroxyhexanenitrile

Refernces

• 1、 Guzzi, Umberto,Ciabatti, Romeo,Padova, Giovanna,Battaglia, Franco,Cellentani, Mario,et al.. "Structure-Activity Studies of 16-Methoxy-16-methyl Prostaglandins". . p. 1826 - 1832. Retrieved 2007/10/02.