Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester
• CAS No.: 193811-96-0
• Molecular Formula: C₄₉H₈₈O₁₀SSi₂
• Molecular Weight: 925.469
• Mol file: 193811-96-0.mol

Synonyms:Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester

Chemical Property of Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester

There total 1 articles about Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl 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:

p-toluenesulfonyl chloride (98-59-9) + (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-Hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-en-1-ol (193811-95-9) → Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester (193811-96-0)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, DMSO, 40 deg C, 30 min, 2.) THF, room temperature, 1 h;

DOI:10.1021/jo970423s

Reference yield:

Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester (193811-96-0) → (+)-asimicin (102989-24-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 86 percent / LiBEt₃H / tetrahydrofuran / 12 h / 0 °C

2: 98 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 12 h

3: 97 percent / I₂, Ph₃P, imidazole / CH₂Cl₂; benzene / 1 h

4: 91 percent / tetrahydrofuran / 12 h / 0 °C

5: 100 percent / (DHQD)2AQN, K₂Fe₃(CN)6, K₂CO₃, K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

6: 19 percent / pyridine / 10 h / Ambient temperature

7: 79 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

8: 1.) BF₃*OEt₂ / 1.) THF, -78 deg C, 10 min, 2.) THF, 20 min

9: i-Pr₂NEt / CH₂Cl₂ / 12 h / Ambient temperature

10: TBAF / tetrahydrofuran / 6 h / 40 °C

11: 2,6-lutidine / tetrahydrofuran / 0.33 h

12: 1.) Pd(PPh₃)4, H₂O, 2.) AgNO₃/SiO₂ / 1.) THF, 1.7 h, 2.) CH₂Cl₂, hexane, 2 h

13: 67 percent / PPTS / ethanol / 16 h / 40 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; K₂Fe₃(CN)6; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; pyridinium p-toluenesulfonate; silica gel; sodium hydride; lithium triethylborohydride; potassium carbonate; silver nitrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; rhodium on alumina; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1021/jo970423s

Reference yield:

Toluene-4-sulfonic acid (E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-enyl ester (193811-96-0) → 2,4,6-Triisopropyl-benzenesulfonic acid (2R,13R)-2-hydroxy-13-(2-trimethylsilanyl-ethoxymethoxy)-13-{(2R,5R,2'R,5'R)-5'-[(R)-1-(2-trimethylsilanyl-ethoxymethoxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl ester (193812-14-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / LiBEt₃H / tetrahydrofuran / 12 h / 0 °C

2: 98 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 12 h

3: 97 percent / I₂, Ph₃P, imidazole / CH₂Cl₂; benzene / 1 h

4: 91 percent / tetrahydrofuran / 12 h / 0 °C

5: 100 percent / (DHQD)2AQN, K₂Fe₃(CN)6, K₂CO₃, K₂OsO₂(OH)4 / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

6: 19 percent / pyridine / 10 h / Ambient temperature

With pyridine; 1H-imidazole; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; K₂Fe₃(CN)6; hydrogen; iodine; lithium triethylborohydride; potassium carbonate; triphenylphosphine; rhodium on alumina; In tetrahydrofuran; dichloromethane; water; ethyl acetate; tert-butyl alcohol; benzene;

DOI:10.1021/jo970423s

upstream raw materials:

p-toluenesulfonyl chloride

(E)-(R)-11-{(2R,5R,2'R,5'R)-5'-[(E)-(R)-11-Hydroxy-1-(2-trimethylsilanyl-ethoxymethoxy)-undec-2-enyl]-octahydro-[2,2']bifuranyl-5-yl}-11-(2-trimethylsilanyl-ethoxymethoxy)-undec-9-en-1-ol

Downstream raw materials:

(+)-asimicin

2,4,6-Triisopropyl-benzenesulfonic acid (2R,13R)-2-hydroxy-13-(2-trimethylsilanyl-ethoxymethoxy)-13-{(2R,5R,2'R,5'R)-5'-[(R)-1-(2-trimethylsilanyl-ethoxymethoxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-tridecyl ester