(3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Base Information

• Chemical Name: (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol
• CAS No.: 73107-73-0
• Molecular Formula: C₂₈H₄₀O₆S
• Molecular Weight: 504.688
• Mol file: 73107-73-0.mol

Synonyms:(3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property of (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

There total 7 articles about (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 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: 100.0%

7-(2-Tetrahydropyranyloxy)-6-<3-(4-methylthiomethylphenyl)-3-(2-tetrahydropyranyloxy)-1-propenyl>-2-oxabicyclo<3.3.0>octan-3-on (73102-81-5,81338-97-8) → (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (73107-73-0)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at -70 ℃; for 6h;

DOI:10.1002/jlac.198219820116

Reference yield:

methyl 4-[(methylsulfanyl)methyl]benzoate (67003-49-0) → (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (73107-73-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) 1,6 M butyllithium / 1) THF, hexane, -78 deg C, 2) -78 deg C, 7h; 20 deg C, 2h

2: 1) 2,2 M BuLi / 1) THF, hexane, 2) 1,2-dimethoxyethane, 1h, 25 deg C

3: 31 percent / aluminumtri-2-propylate / toluene / 6 h / 80 °C

4: K₂CO₃ / ethanol / 1.5 h / 25 °C

5: 2percent 4-toluol sulfonic acid / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

6: 100 percent / 70percent Na-dihydridobis(2-methoxyethoxy)aluminat / toluene / 6 h / -70 °C

With n-butyllithium; aluminum isopropoxide; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1002/jlac.198219820116

Reference yield:

2<4-Methylthiomethylphenyl>-2-oxoethylphosphonsaeure-dimethylester (73102-75-7) → (3aS,5S,6aR)-4-[(E)-3-(4-Methylsulfanylmethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (73107-73-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) 2,2 M BuLi / 1) THF, hexane, 2) 1,2-dimethoxyethane, 1h, 25 deg C

2: 31 percent / aluminumtri-2-propylate / toluene / 6 h / 80 °C

3: K₂CO₃ / ethanol / 1.5 h / 25 °C

4: 2percent 4-toluol sulfonic acid / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

5: 100 percent / 70percent Na-dihydridobis(2-methoxyethoxy)aluminat / toluene / 6 h / -70 °C

With n-butyllithium; aluminum isopropoxide; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1002/jlac.198219820116

upstream raw materials:

7-(2-Tetrahydropyranyloxy)-6-<3-(4-methylthiomethylphenyl)-3-(2-tetrahydropyranyloxy)-1-propenyl>-2-oxabicyclo<3.3.0>octan-3-on

methyl 4-[(methylsulfanyl)methyl]benzoate

2<4-Methylthiomethylphenyl>-2-oxoethylphosphonsaeure-dimethylester

7-Hydroxy-6-<3-hydroxy-3-(4-methylthiomethylphenyl)-1-propenyl>-2-oxabicyclo<3.3.0>octan-3-on

Downstream raw materials:

(5Z,9α,11α,13E)-9,11,13-Trihydroxy-15-(4-methylthiomethylphenyl)-16,17,18,19,20-pentaprosta-5,14-dien-1-saeure

(5Z,9α,11α,13E)-9-Hydroxy-15-(4-methylthiomethylphenyl)-11,15-bis(2-tetrahydropyranyloxy)-16,17,18,19,20-pentanorprosta-5,13-dien-1-saeure