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

Base Information

• Chemical Name: (5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid t-butyl ester
• CAS No.: 170290-77-4
• Molecular Formula: C₃₄H₅₈O₈
• Molecular Weight: 594.83

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

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

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

There total 1 articles about (5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic 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: 86.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-2,3,4,16,17,18,19,20-octanor-9-hydroxy-5-prostenol (467253-89-0) → (5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid t-butyl ester (170290-77-4)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In water; toluene; for 0.666667h;

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

Reference yield: 96.0%

isopropyl alcohol (67-63-0,8013-70-5) + (5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid t-butyl ester (170290-77-4) → (5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid isopropyl ester (170290-80-9)

Guidance literature:

With titanium(IV) isopropylate; for 1h; Heating;

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

Reference yield: 34.0%

(5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid t-butyl ester (170290-77-4) → (5Z)-(9R,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-9-chloro-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid t-butyl ester (170290-78-5) + {(Z)-4-[(4R,5R)-2-Chloro-5-[(R)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enyl]-but-2-enyloxy}-acetic acid tert-butyl ester

Guidance literature:

With tetrachloromethane; triphenylphosphine; In pyridine; acetonitrile; for 17h;

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

upstream raw materials:

bromoacetic acid tert-butyl ester

(5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-2,3,4,16,17,18,19,20-octanor-9-hydroxy-5-prostenol

Downstream raw materials:

(5Z)-(9S,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid isopropyl ester

(5Z)-(9R,11R,15R)-11,15-bis(tetrahydropyran-2-yloxy)-9-chloro-15-cyclohexyl-3-oxa-16,17,18,19,20-pentanor-5-prostenoic acid t-butyl ester

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