5-Hexenoic acid, 3-[(4-methoxyphenyl)methoxy]-4-methyl-, (1S,2R,3R,4E,7S)-1-ethenyl-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2 ,4,8-trimethyl-4-nonen-1-yl ester, (3R,4S)-

Base Information

• Chemical Name: 5-Hexenoic acid, 3-[(4-methoxyphenyl)methoxy]-4-methyl-, (1S,2R,3R,4E,7S)-1-ethenyl-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2 ,4,8-trimethyl-4-nonen-1-yl ester, (3R,4S)-
• CAS No.: 929568-38-7
• Molecular Formula: C37H52O7
• Molecular Weight: 608.816
• Mol file: 929568-38-7.mol

Synonyms:

Chemical Property of 5-Hexenoic acid, 3-[(4-methoxyphenyl)methoxy]-4-methyl-, (1S,2R,3R,4E,7S)-1-ethenyl-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2 ,4,8-trimethyl-4-nonen-1-yl ester, (3R,4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Hexenoic acid, 3-[(4-methoxyphenyl)methoxy]-4-methyl-, (1S,2R,3R,4E,7S)-1-ethenyl-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2 ,4,8-trimethyl-4-nonen-1-yl ester, (3R,4S)-

There total 13 articles about 5-Hexenoic acid, 3-[(4-methoxyphenyl)methoxy]-4-methyl-, (1S,2R,3R,4E,7S)-1-ethenyl-3-hydroxy-7-[(4-methoxyphenyl)methoxy]-2 ,4,8-trimethyl-4-nonen-1-yl ester, (3R,4S)- 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: 96.0%

(3R,4S)-3-(4-methoxybenzyloxy)-4-methyl-5-hexenal (902132-11-0) + (3S,5E,8S,9S)-9-hydroxy-3-(4-methoxybenzyloxy)-2,6,8-trimethylundeca-5,10-dien-7-one (929568-37-6) → (3S,5E,7R,8R,9S)-9-[(3R,4S)-3-(4-methoxybenzyloxy)-4-methyl-hex-5-enoyloxy]-3-(4-methoxybenzyloxy)-2,6,8-trimethylundeca-5,10-dien-7-ol (929568-38-7)

Guidance literature:

(PhCHO)2SmI*SmI₃; In tetrahydrofuran; for 0.5h;

DOI:10.1021/ol062932z

Reference yield:

(4S,5S)-5-(tert-butyldimethylsilyloxy)-2-(diethoxyphosphoryl)-4-methylhept-6-en-3-one (913288-85-4) → (3S,5E,7R,8R,9S)-9-[(3R,4S)-3-(4-methoxybenzyloxy)-4-methyl-hex-5-enoyloxy]-3-(4-methoxybenzyloxy)-2,6,8-trimethylundeca-5,10-dien-7-ol (929568-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h

1.2: 87 percent / tetrahydrofuran; H₂O / 24 h / 20 °C

2.1: 93 percent / aq. HF / acetonitrile / 0.25 h / 20 °C

3.1: 96 percent / (PhCHO)2SmI*SmI₃ / tetrahydrofuran / 0.5 h

With barium dihydroxide; hydrogen fluoride; (PhCHO)2SmI*SmI₃; In tetrahydrofuran; acetonitrile; 1.2: Horner-Wadsworth-Emmons reaction / 3.1: Evans-Tishchenko reaction;

DOI:10.1021/ol062932z

Reference yield:

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-4-enethioic acid S-{(1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl} ester (913288-90-1) → (3S,5E,7R,8R,9S)-9-[(3R,4S)-3-(4-methoxybenzyloxy)-4-methyl-hex-5-enoyloxy]-3-(4-methoxybenzyloxy)-2,6,8-trimethylundeca-5,10-dien-7-ol (929568-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: nBuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 81 percent / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h

2.2: 87 percent / tetrahydrofuran; H₂O / 24 h / 20 °C

3.1: 93 percent / aq. HF / acetonitrile / 0.25 h / 20 °C

4.1: 96 percent / (PhCHO)2SmI*SmI₃ / tetrahydrofuran / 0.5 h

With barium dihydroxide; n-butyllithium; hydrogen fluoride; (PhCHO)2SmI*SmI₃; In tetrahydrofuran; hexane; acetonitrile; 2.2: Horner-Wadsworth-Emmons reaction / 4.1: Evans-Tishchenko reaction;

DOI:10.1021/ol062932z

upstream raw materials:

(3R,4S)-3-(4-methoxybenzyloxy)-4-methyl-5-hexenal

(3S,5E,8S,9S)-9-hydroxy-3-(4-methoxybenzyloxy)-2,6,8-trimethylundeca-5,10-dien-7-one

(4S,5S)-5-(tert-butyldimethylsilyloxy)-2-(diethoxyphosphoryl)-4-methylhept-6-en-3-one

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pent-4-enethioic acid S-{(1S,2R)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl} ester