(Z)-4-[(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]-but-2-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-4-[(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]-but-2-enoic acid methyl ester
• CAS No.: 130172-78-0
• Molecular Formula: C₃₅H₆₀O₇Si
• Molecular Weight: 620.943

Synonyms:

Chemical Property of (Z)-4-[(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]-but-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-4-[(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]-but-2-enoic acid methyl ester

There total 1 articles about (Z)-4-[(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]-but-2-enoic 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:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + [(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 (120891-38-5) → (Z)-4-[(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]-but-2-enoic acid methyl ester (130172-78-0) + (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 (170552-02-0)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -70 ℃; for 0.5h; Product distribution; other phosphonates, other bases;

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

Reference yield:

(Z)-4-[(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]-but-2-enoic acid methyl ester (130172-78-0) → (Z)-4-[(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]-but-2-en-1-ol + (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)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -70 - -20 ℃; for 2h; Title compound not separated from byproducts;

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

Reference yield:

(Z)-4-[(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]-but-2-enoic acid methyl ester (130172-78-0) → {(Z)-4-[(4R,5R)-5-[(E)-(S)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propenyl]-4-(tetrahydro-pyran-2-yloxy)-cyclopent-1-enyl]-but-2-enyloxy}-acetic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAH / toluene / 2 h / -70 - -20 °C

2: 25percent NaOH, Bu₄NHSO₄ / toluene / 15 h / 24 °C

3: TsCl, Bu₄NCl

With sodium hydroxide; tetrabutyl-ammonium chloride; tetra(n-butyl)ammonium hydrogensulfate; diisobutylaluminium hydride; p-toluenesulfonyl chloride; In toluene;

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

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

[(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

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-prostadienol

ZK 118182

{(Z)-4-[(4R,5R)-5-((E)-(S)-3-Cyclohexyl-3-hydroxy-propenyl)-4-hydroxy-cyclopent-1-enyl]-but-2-enyloxy}-acetic acid tert-butyl ester

ZK 118882

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