(Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol

Base Information

• Chemical Name: (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol
• CAS No.: 885674-91-9
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• Mol file: 885674-91-9.mol

Synonyms:(Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol

Chemical Property of (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol

There total 6 articles about (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-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:

Triethyl-{(Z)-(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-hex-3-en-5-ynyloxy}-silane (885674-89-5) → (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol (885674-91-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; water; acetic acid; at 20 ℃; for 48h;

DOI:10.1002/ejoc.200500675

Reference yield:

(S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-pentanal (885674-88-4) → (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol (885674-91-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHMDS; HMPA / tetrahydrofuran / -78 - 20 °C

2: Pd(PPh₃)4 / tetrahydrofuran / 2 h / 20 °C

3: TBAF*H₂O / tetrahydrofuran; H₂O; acetic acid / 48 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; acetic acid; 1: Stork-Zhao olefination / 2: Negishi coupling;

DOI:10.1002/ejoc.200500675

Reference yield:

Triethyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-but-3-enyloxy}-silane (885675-21-8) → (Z)-(S)-1-(4-Methoxy-benzyloxy)-2,2-dimethyl-oct-5-en-7-yn-3-ol (885674-91-9)

Guidance literature:

Multi-step reaction with 4 steps

1: O₃; PPh₃ / CH₂Cl₂ / -78 - 20 °C

2: NaHMDS; HMPA / tetrahydrofuran / -78 - 20 °C

3: Pd(PPh₃)4 / tetrahydrofuran / 2 h / 20 °C

4: TBAF*H₂O / tetrahydrofuran; H₂O; acetic acid / 48 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; ozone; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; acetic acid; 2: Stork-Zhao olefination / 3: Negishi coupling;

DOI:10.1002/ejoc.200500675

upstream raw materials:

Triethyl-{(Z)-(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-hex-3-en-5-ynyloxy}-silane

(S)-5-(4-Methoxy-benzyloxy)-4,4-dimethyl-3-triethylsilanyloxy-pentanal

Triethyl-{(S)-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-but-3-enyloxy}-silane

Triethyl-{(Z)-(S)-4-iodo-1-[2-(4-methoxy-benzyloxy)-1,1-dimethyl-ethyl]-but-3-enyloxy}-silane

Downstream raw materials:

2-[(3E,7Z)-(2R,10S)-10-Hydroxy-2-methoxy-12-(4-methoxy-benzyloxy)-11,11-dimethyl-dodeca-3,7-dien-5-ynyl]-oxazole-4-carboxylic acid methyl ester

C₆₁H₈₀N₂O₁₃Si