(7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Base Information

• Chemical Name: (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione
• CAS No.: 566203-38-1
• Molecular Formula: C₂₈H₃₈O₁₁
• Molecular Weight: 550.603
• Mol file: 566203-38-1.mol

Synonyms:(7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Chemical Property of (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

There total 11 articles about (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione 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: 65.0%

(-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate (566203-39-2) → (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (566203-38-1)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride; In 1,2-dichloro-ethane; at 80 ℃; for 120h;

DOI:10.1021/ol0350689

Reference yield: 65.0%

(-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate (566203-39-2) → (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (566203-38-1) + (E)-(4R,5S)-4-(2-Methoxy-ethoxymethoxy)-5-[(E)-(3-phenyl-acryloyl)oxy]-hex-2-enoic acid (S)-2-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-but-3-enyloxycarbonyl]-1-methyl-ethyl ester

Guidance literature:

In 1,2-dichloro-ethane; at 80 ℃; for 120h;

DOI:10.1021/jo035435u

Reference yield:

(3R,4S)-4-(tert-butyldimethylsilanyloxy)-pent-1-en-3-ol (132055-83-5) → (7E,13E)-(4S,9R,10S,15R,16S)-15-(4-Methoxy-benzyloxy)-9-(2-methoxy-ethoxymethoxy)-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (566203-38-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 47 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h / 20 °C

2.1: 96 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

3.1: 99 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 95 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C

5.2: 99 percent / 4-(dimethylamino)pyridine / toluene / 1 h

6.1: 85 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 120 h / 20 °C

7.1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

8.1: 65 percent / 1,2-dichloro-ethane / 120 h / 80 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo035435u

upstream raw materials:

(-)-1-[3-(4-methoxybenzyloxy)-1-penten-4-yloxycarbonyl]prop-2-yl 5-acryloyloxy-4-[(2-methoxyethoxy)methoxy]-2-hexenoate

4-methoxybenzyl 2,2,2-trifluoroacetimidate

(3R,4S)-4-(tert-butyldimethylsilanyloxy)-pent-1-en-3-ol

(3R,4S)-4-hydroxy-3-(4-methoxybenzyloxy)-1-pentene

Downstream raw materials:

(+)-macrosphelide A