(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-prostadienoic acid methyl ester

Base Information

Chemical Name:(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-prostadienoic acid methyl ester
CAS No.:170552-02-0
Molecular Formula:C₃₅H₆₀O₇Si
Molecular Weight:620.943
Hs Code.:

(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-prostadienoic acid methyl ester

Synonyms:(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-prostadienoic acid methyl ester

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Chemical Property of (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-prostadienoic acid methyl ester

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Technology Process of (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-prostadienoic acid methyl ester

There total 6 articles about (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-prostadienoic acid methyl 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: 84.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 170290-96-7
(5E,13E)-(9S,11R,15S)-11,15-bis(tetrahydropyran-2-yloxy)-15-cyclohexyl-9-hydroxy-2,3,4,16,17,18,19,20-octanor-5,13-prostadienoic acid methyl ester

: 170552-02-0
(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-prostadienoic acid methyl ester

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 1h;
DOI:10.1016/S0968-0896(02)00016-0

Reference yield:

: 120962-75-6
[3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-(tetrahydropyran-2-yloxy)-1-propenyl]-5-(tetrahydropyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

: 170552-02-0
(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-prostadienoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaOH / methanol / 22 h / 24 °C

2: tetrahydrofuran; dimethylsulfoxide / 16 h / 24 °C

3: imidazole / dimethylformamide / 4 h / 24 °C

4: 79 percent / DIBAH / toluene / 2 h / -70 °C

5: KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / -70 °C

With 1H-imidazole; sodium hydroxide; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)97413-6

Reference yield:

: [(1R,2R,3R,5S)-2-[(E)-(S)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid

: 170552-02-0
(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-prostadienoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: tetrahydrofuran; dimethylsulfoxide / 16 h / 24 °C

2: imidazole / dimethylformamide / 4 h / 24 °C

3: 79 percent / DIBAH / toluene / 2 h / -70 °C

4: KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / -70 °C

With 1H-imidazole; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)97413-6