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

Base Information

• Chemical Name: (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoic acid
• CAS No.: 85548-84-1
• Molecular Formula: C₃₈H₆₅NO₇SSi₂
• Molecular Weight: 736.174
• Mol file: 85548-84-1.mol

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

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

There total 5 articles about (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-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: 89.0%

(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (77494-48-5) → C39H67NO7SSi2 (85453-63-0) + (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (85548-84-1)

Guidance literature:

With peracetic acid; sodium tungstate; sodium carbonate; In methanol; water; at 25 ℃; for 10h;

DOI:10.1021/jo00161a010

Reference yield: 85.0%

(5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(methylamino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (77494-48-5) → (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (85548-84-1)

Guidance literature:

With peracetic acid; sodium tungstate; In methanol;

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 (77494-47-4) → (5Z,13E,8R,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-8-(phenylsulfonyl)-5,13-prostadienoic acid (85548-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / sodium hydroxide / methanol; H₂O / 48 h / 25 °C

2: 85 percent / 40percent peracetic acid, sodium tungstate / methanol

With peracetic acid; sodium hydroxide; sodium tungstate; In methanol; water;

DOI:10.1021/ja00398a048

upstream raw materials:

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

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:

prostaglandin A₂

dinoprostone