(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol

Base Information

• Chemical Name: (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol
• CAS No.: 623926-34-1
• Molecular Formula: C₂₄H₃₈O₅
• Molecular Weight: 406.563
• Mol file: 623926-34-1.mol

Synonyms:(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol

Chemical Property of (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol

There total 11 articles about (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-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: 90.0%

(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether (444682-16-0) → (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol (623926-34-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/ol026084t

Reference yield:

(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol (106296-58-6) → (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol (623926-34-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

2.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

2.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

3.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

4.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 3.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(2S,3S,4S)-1-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethyl hex-5-ene (184291-95-0) → (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-ol (623926-34-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

1.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

2.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

2.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

3.1: 89 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; ozone; In tetrahydrofuran; methanol; dichloromethane; 2.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

upstream raw materials:

(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether

2-(4-iodobutoxy)tetrahydropyran

{4-[(tetrahydropyran-2-yl)oxy]butyl}(triphenyl)phosphonium iodide

(2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol

Downstream raw materials:

(4-methoxybenzyloxy)acetic acid (Z,Z,Z)-(6S,7S,8S,13S,14S,15S,16S)-15-carbamoyloxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane

[(6Z,11Z)-(1S,2S,3S,8S,9S,10S)-3,9-Bis-(4-methoxy-benzyloxy)-2,8,10-trimethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-15-(tetrahydro-pyran-2-yloxy)-pentadeca-6,11-dienyloxy]-tert-butyl-dimethyl-silane

Carbamic acid (4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1S,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyl ester