4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 394657-50-2
• Molecular Formula: C₅₀H₇₆O₁₀Si
• Molecular Weight: 865.233
• Mol file: 394657-50-2.mol

Synonyms:4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester

There total 38 articles about 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl 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: 64.0%

{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-(4-Methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde + (diphenoxy-phosphoryl)acetic acid 2-trimethylsilanyl-ethyl ester (394657-61-5) → 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester (394657-50-2)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo010854h

Reference yield:

(S)-4-Methyl-1-(tetrahydro-pyran-2-yloxy)-pent-4-en-2-ol (289472-93-1) → 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester (394657-50-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 100 percent / KH; 18-crown-6 / tetrahydrofuran / 0 - 23 °C

2.1: Cl₂(PCy₃₀₂Ru=CHPh / CH₂Cl₂ / 2 h / 23 °C

3.1: 3.96 g / CSA / methanol / 1 h

4.1: 85 percent / DMSO; (COCl)2; iPr₂NEt / CH₂Cl₂ / -78 - 23 °C

5.1: 67 percent / PPh₃ / CH₂Cl₂ / 0 - 23 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 23 °C

6.2: 64 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

8.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

9.1: 81 percent / Red-Al / tetrahydrofuran / -40 - -20 °C

10.1: PPTS / CH₂Cl₂ / 12 h / 23 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

12.1: 11 mg / KN(TMS)2; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

With n-butyllithium; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; potassium hydride; potassium hexamethylsilazane; L-Selectride; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4.1: Swern oxidation / 13.1: Horner-Emmons reaction;

DOI:10.1021/jo010854h

Reference yield:

(2S)-2-(2-allyloxy-4-methyl-pent-4-enyloxy)-tetrahydropyran (289472-94-2) → 4-{6-[10-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-11-(tetrahydro-pyran-2-yloxy)-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 2-trimethylsilanyl-ethyl ester (394657-50-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Cl₂(PCy₃₀₂Ru=CHPh / CH₂Cl₂ / 2 h / 23 °C

2.1: 3.96 g / CSA / methanol / 1 h

3.1: 85 percent / DMSO; (COCl)2; iPr₂NEt / CH₂Cl₂ / -78 - 23 °C

4.1: 67 percent / PPh₃ / CH₂Cl₂ / 0 - 23 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 23 °C

5.2: 64 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / 23 °C

7.1: 87 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

8.1: 81 percent / Red-Al / tetrahydrofuran / -40 - -20 °C

9.1: PPTS / CH₂Cl₂ / 12 h / 23 °C

10.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

11.1: 11 mg / KN(TMS)2; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

With n-butyllithium; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; L-Selectride; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 3.1: Swern oxidation / 12.1: Horner-Emmons reaction;

DOI:10.1021/jo010854h

upstream raw materials:

(diphenoxy-phosphoryl)acetic acid 2-trimethylsilanyl-ethyl ester

[(2R,4S)-4-(1-Ethoxy-allyloxy)-2-methyl-hept-6-enyloxymethyl]-benzene

3,4-dihydro-2H-pyran

[3R]-4-Benzyloxy-3-methylbutanal