4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

Base Information

Chemical Name:4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid
CAS No.:349539-73-7
Molecular Formula:C₄₀H₅₄O₉
Molecular Weight:678.863
Hs Code.:

4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

Synonyms:4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

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Chemical Property of 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

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Technology Process of 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

There total 38 articles about 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid 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: 74.0%

: 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid methyl ester

: 349539-73-7
4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; water;
DOI:10.1016/S0040-4039(01)00436-1

Reference yield:

: 289472-94-2
(2S)-2-(2-allyloxy-4-methyl-pent-4-enyloxy)-tetrahydropyran

: 349539-73-7
4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

Guidance literature:: Multi-step reaction with 19 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: TFA / CH₂Cl₂ / 1 h / 23 °C

10.1: 71 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

11.1: 74 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

12.1: PPTS / CH₂Cl₂ / 5 h / 23 °C

13.1: 102 mg / TBAF / tetrahydrofuran / 3 h / 23 °C

14.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

15.1: 89 percent / Ph₃P; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

16.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h

16.2: 75 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

17.1: CSA / methanol

18.1: 22 mg / LiOH / tetrahydrofuran; H₂O / 2 h

With lithium hydroxide; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 3.1: Swern oxidation;
DOI:10.1021/jo010854h

Reference yield:

: 289472-93-1
(S)-4-Methyl-1-(tetrahydro-pyran-2-yloxy)-pent-4-en-2-ol

: 349539-73-7
4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-10-Hydroxy-11-(4-methoxy-benzyloxy)-6-methoxymethoxy-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

Guidance literature:: Multi-step reaction with 20 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: TFA / CH₂Cl₂ / 1 h / 23 °C

11.1: 71 percent / CSA / CH₂Cl₂ / 0.5 h / 23 °C

12.1: 74 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

13.1: PPTS / CH₂Cl₂ / 5 h / 23 °C

14.1: 102 mg / TBAF / tetrahydrofuran / 3 h / 23 °C

15.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

16.1: 89 percent / Ph₃P; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

17.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h

17.2: 75 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

18.1: CSA / methanol

19.1: 22 mg / LiOH / tetrahydrofuran; H₂O / 2 h

With lithium hydroxide; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium hydride; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; trifluoroacetic acid; Grubbs catalyst first generation; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 4.1: Swern oxidation;
DOI:10.1021/jo010854h