2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

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Chemical Name:2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid
CAS No.:624727-41-9
Molecular Formula:C₂₉H₄₀O₈
Molecular Weight:516.632
Hs Code.:

Synonyms:2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

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Chemical Property of 2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

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Technology Process of 2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

There total 13 articles about 2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic 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: 91.0%

: 624727-39-5
methyl 2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoate

: 2-Methoxy-6-((E)-(S)-5-{(4R,6R)-6-[2-(4-methoxy-benzyloxy)-ethyl]-[1,3]dioxan-4-yl}-hex-2-enyl)-benzoic acid

: 624727-41-9
2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; at 70 ℃; for 72h;
DOI:10.1021/jo035054g

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 624727-41-9
2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: 80 percent / SnCl₂ / CH₂Cl₂ / 1 h / 20 °C

2.1: H₂; (R)-(+)-BINAP / [RuCl₂(PhH)]2 / dimethylformamide / 20 h / 90 °C / 3000.24 Torr

3.1: imidazole; DMAP / dimethylformamide / 48 h

4.1: DIBAH / CH₂Cl₂; hexane / 3.5 h / -78 °C

5.1: 5.67 g / TiCl₄; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

6.1: 81 percent / (iPr)2NEt; tetrabutylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

7.1: 77 percent / LiBH₄ / methanol; tetrahydrofuran / 20 °C

8.1: 98 percent / pyridine / 2 h / 0 °C

9.1: 84 percent / NaI; DBU / various solvent(s) / 3 h / Heating

10.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

10.2: 65 percent / Cs₂CO₃; aq. AsPh₃; PdCl₂(dppf) / tetrahydrofuran / 12 h

11.1: 100 percent / TBAF / tetrahydrofuran / 48 h

12.1: 91 percent / aq. LiOH / tetrahydrofuran; methanol / 72 h / 70 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; sodium iodide; tin(ll) chloride; (-)-sparteine; dichloro(benzene)ruthenium(II) dimer; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035054g

Reference yield:

: 105-13-5
4-Methoxybenzyl alcohol

: 624727-41-9
2-[(2E,5S,6R,8R)-8-hydroxy-10-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-5-methyldec-2-enyl]-6-methoxybenzoic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: ClCH₂CO₂H; aq. NaOH; acetic acid / 144 h / 40 °C

2.1: 80 percent / SnCl₂ / CH₂Cl₂ / 1 h / 20 °C

3.1: H₂; (R)-(+)-BINAP / [RuCl₂(PhH)]2 / dimethylformamide / 20 h / 90 °C / 3000.24 Torr

4.1: imidazole; DMAP / dimethylformamide / 48 h

5.1: DIBAH / CH₂Cl₂; hexane / 3.5 h / -78 °C

6.1: 5.67 g / TiCl₄; (-)-sparteine / CH₂Cl₂ / 1 h / 0 °C

7.1: 81 percent / (iPr)2NEt; tetrabutylammonium iodide / CH₂Cl₂ / 72 h / 20 °C

8.1: 77 percent / LiBH₄ / methanol; tetrahydrofuran / 20 °C

9.1: 98 percent / pyridine / 2 h / 0 °C

10.1: 84 percent / NaI; DBU / various solvent(s) / 3 h / Heating

11.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

11.2: 65 percent / Cs₂CO₃; aq. AsPh₃; PdCl₂(dppf) / tetrahydrofuran / 12 h

12.1: 100 percent / TBAF / tetrahydrofuran / 48 h

13.1: 91 percent / aq. LiOH / tetrahydrofuran; methanol / 72 h / 70 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; tetrabutyl ammonium fluoride; hydrogen; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; chloroacetic acid; sodium iodide; tin(ll) chloride; (-)-sparteine; dichloro(benzene)ruthenium(II) dimer; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035054g