2-{(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}-ethanol

Base Information

• Chemical Name: 2-{(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}-ethanol
• CAS No.: 349539-62-4
• Molecular Formula: C₄₃H₆₄O₉
• Molecular Weight: 724.976

Synonyms:2-{(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}-ethanol

Chemical Property of 2-{(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}-ethanol

Chemical Property:

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Technology Process of 2-{(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}-ethanol

There total 37 articles about 2-{(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}-ethanol 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: 76.0%

tert-butyl-(2-{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}-ethoxy)-dimethyl-silane → 2-{(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}-ethanol (349539-62-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)00436-1

Reference yield:

(S)-4-Methyl-1-(tetrahydro-pyran-2-yloxy)-pent-4-en-2-ol (289472-93-1) → 2-{(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}-ethanol (349539-62-4)

Guidance literature:

Multi-step reaction with 12 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: 14.5 mg / TBAF / tetrahydrofuran / 2 h / 23 °C

With n-butyllithium; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; 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; 4.1: Swern oxidation;

DOI:10.1021/jo010854h

Reference yield:

(2S)-2-(2-allyloxy-4-methyl-pent-4-enyloxy)-tetrahydropyran (289472-94-2) → 2-{(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}-ethanol (349539-62-4)

Guidance literature:

Multi-step reaction with 11 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: 14.5 mg / TBAF / tetrahydrofuran / 2 h / 23 °C

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; 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; 3.1: Swern oxidation;

DOI:10.1021/jo010854h

upstream raw materials:

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

3,4-dihydro-2H-pyran

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

(2S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde

Downstream raw materials:

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-ethoxymethyl ester

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