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

Base Information

• Chemical Name: Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate
• CAS No.: 85548-77-2
• Molecular Formula: C₄₁H₇₃NO₆SSi₂
• Molecular Weight: 764.271

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 2 articles about Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate 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:

methyl (5Z)-7-bromo-5-heptenoate (51751-83-8) + (S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene (41138-68-5) + (1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene (77493-70-0) → Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (85548-77-2) + Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77506-98-0) + (1S,2S,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-trans-2-(phenylsulfonyl)cyclopentane (77494-46-3) + (1S,2R,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-cis-2-(phenylsulfonyl)cyclopentane (77520-22-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo00161a010

Reference yield:

(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene (41138-67-4) + methyl (5Z)-7-iodo-5-heptenoate (64493-06-7) + (1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene (77493-70-0) → Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (85548-77-2) + Methyl (5Z,13E,8R,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (77506-98-0) + (1S,2S,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-trans-2-(phenylsulfonyl)cyclopentane (77494-46-3) + (1S,2R,3S,4R)-cis-4-(tert-Butyldimethylsiloxy)-trans-3-<(E,S)-3'-(tert-butyldimethylsiloxy)-1'-octenyl>-1-(dimethylamino)-cis-2-(phenylsulfonyl)cyclopentane (77520-22-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo00161a010

Reference yield: 86.0%

Methyl (5Z,13E,8S,9S,11R,12S,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(dimethylamino)-8-(phenylsulfonyl)-5,13-prostadienoate (85548-77-2) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → (Z)-7-{(1S,2S,3R,5S)-1-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-[methyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-cyclopentyl}-hept-5-enoic acid methyl ester (85548-86-3)

Guidance literature:

With sodium hydrogencarbonate; at 25 ℃; for 120h;

DOI:10.1021/jo00161a010

upstream raw materials:

methyl (5Z)-7-bromo-5-heptenoate

(S,E)-3-t-butyldimethylsilyloxy-1-lithio-1-octene

(1S,4R)-cis-4-(tert-Butyldimethylsiloxy)-1-(dimethylamino)-2-(phenylsulfonyl)-2-cyclopentene

(1E,3S)-1-iodo-3-(tert-butyldimethylsiloxy)-1-octene

Downstream raw materials:

(Z)-7-{(1S,2S,3R,5S)-1-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-[methyl-(2,2,2-trichloro-ethoxycarbonyl)-amino]-cyclopentyl}-hept-5-enoic acid methyl ester

prostaglandin A₂

dinoprostone

(Z)-7-{(1S,2S,3R,5S)-1-Benzenesulfonyl-3-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-methylamino-cyclopentyl}-hept-5-enoic acid methyl ester

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