(S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one

Base Information

• Chemical Name: (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one
• CAS No.: 862557-76-4
• Molecular Formula: C₃₉H₅₀O₄Si
• Molecular Weight: 610.909
• Mol file: 862557-76-4.mol

Synonyms:(S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one

Chemical Property of (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one

There total 4 articles about (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one 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: 68.0%

((E)-8-Benzyloxy-oct-4-enyl)-triphenyl-phosphonium; iodide + (S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde (182072-78-2) → (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one (862557-76-4)

Guidance literature:

((E)-8-Benzyloxy-oct-4-enyl)-triphenyl-phosphonium; iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

(S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 - 0 ℃; for 3.5h;

DOI:10.1021/jo050697c

Reference yield:

((E)-8-Iodo-oct-4-enyloxymethyl)-benzene (862558-02-9) → (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one (862557-76-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / NaHCO₃ / acetonitrile / 8 h / Heating

2.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: 68 percent / HMPA / tetrahydrofuran / 3.5 h / -78 - 0 °C

With sodium hexamethyldisilazane; sodium hydrogencarbonate; In tetrahydrofuran; acetonitrile; 2.2: Wittig reaction;

DOI:10.1021/jo050697c

Reference yield:

ethyl (4E)-8-benzyloxy-4-enoctanoate (181803-05-4) → (S)-5-[(4Z,8E)-(S)-12-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-dodeca-4,8-dienyl]-dihydro-furan-2-one (862557-76-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / LiAlH₄ / diethyl ether / 3 h / Heating

2.1: 90 percent / iodine; imidazole; PPh₃ / CH₂Cl₂ / 0.5 h

3.1: 80 percent / NaHCO₃ / acetonitrile / 8 h / Heating

4.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

4.2: 68 percent / HMPA / tetrahydrofuran / 3.5 h / -78 - 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; 4.2: Wittig reaction;

DOI:10.1021/jo050697c

upstream raw materials:

(S)-4-(tert-Butyl-diphenyl-silanyloxy)-4-((S)-5-oxo-tetrahydro-furan-2-yl)-butyraldehyde

((E)-8-Iodo-oct-4-enyloxymethyl)-benzene

ethyl (4E)-8-benzyloxy-4-enoctanoate

(E)-8-(benzyloxy)oct-4-en-1-ol

Downstream raw materials:

Methanesulfonic acid (E)-(R)-8-benzyloxy-1-((2S,5S,2'S)-5'-oxo-octahydro-[2,2']bifuranyl-5-yl)-oct-4-enyl ester

(2S,2'R,5'R,2''S,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

(2S,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one

(S)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one