[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

Base Information

• Chemical Name: [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester
• CAS No.: 120891-36-3
• Molecular Formula: C₃₃H₅₈O₇Si
• Molecular Weight: 594.905

Synonyms:[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

Chemical Property of [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

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Technology Process of [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

There total 3 articles about [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic 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:

[(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 methyl ester (120891-37-4) + tert-butyldimethylsilyl chloride (18162-48-6) → [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester (120891-36-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 24 ℃; for 4h;

DOI:10.1016/S0040-4039(00)97413-6

Reference yield:

[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 (120962-75-6) → [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester (120891-36-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOH / methanol / 22 h / 24 °C

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

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

With 1H-imidazole; sodium hydroxide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

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 → [(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester (120891-36-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97413-6

upstream raw materials:

[(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 methyl ester

tert-butyldimethylsilyl chloride

[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

Downstream raw materials:

(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

[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde

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