(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid

Base Information

• Chemical Name: (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid
• CAS No.: 77494-48-5
• Molecular Formula: C₃₉H₆₉NO₆SSi₂
• Molecular Weight: 736.217
• Mol file: 77494-48-5.mol

Synonyms:(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid

Chemical Property of (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid

There total 3 articles about (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid 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: 99.0%

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77494-47-4) → (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (77494-48-5)

Guidance literature:

With sodium hydroxide; In methanol; water; at 25 ℃; for 48h;

DOI:10.1021/ja00398a048

Reference yield:

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-<methylamino>-8-(phenylsulfonyl)-5,13-prostadienoate (77506-99-1) → (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (77494-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / activated zinc / tetrahydrofuran

2: 99 percent / sodium hydroxide / methanol; H₂O / 48 h / 25 °C

With sodium hydroxide; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00398a048

Reference yield:

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77506-98-0) → (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (77494-48-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / sodium bicarbonate / 72 h / 25 °C

2: 92 percent / activated zinc / tetrahydrofuran

3: 99 percent / sodium hydroxide / methanol; H₂O / 48 h / 25 °C

With sodium hydroxide; sodium hydrogencarbonate; zinc; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00398a048

upstream raw materials:

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoate

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate

Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-<methylamino>-8-(phenylsulfonyl)-5,13-prostadienoate

Downstream raw materials:

dinoprostone

prostaglandin A₂

(5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoic acid

C₃₉H₆₇NO₇SSi₂