(5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester

Base Information

• Chemical Name: (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester
• CAS No.: 170552-03-1
• Molecular Formula: C₄₀H₇₀O₈Si
• Molecular Weight: 707.076

Synonyms:

Chemical Property of (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester

Chemical Property:

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Technology Process of (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester

There total 1 articles about (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl 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: 48.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-2,3,4,16,17,18,19,20-octanor-5,13-prostadienol (170290-97-8) → (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester (170552-03-1)

Guidance literature:

With sodium hydroxide; n-Bu₄HSO₄; In water; toluene;

DOI:10.1016/S0968-0896(02)00016-0

Reference yield: 38.0%

(5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester (170552-03-1) → (5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester (130274-01-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;

DOI:10.1016/S0968-0896(02)00016-0

upstream raw materials:

bromoacetic acid tert-butyl ester

(5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-9-(t-butyldimethylsiloxy)-15-cyclohexyl-2,3,4,16,17,18,19,20-octanor-5,13-prostadienol

Downstream raw materials:

(5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5,13-prostadienoic acid t-butyl ester

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