(2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester

Base Information

• Chemical Name: (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester
• CAS No.: 185909-52-8
• Molecular Formula: C₂₄H₃₄O₆
• Molecular Weight: 418.53

Synonyms:(2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester

Chemical Property of (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester

There total 10 articles about (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester 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: 83.0%

(E)-3-hydroxyprop-1-enylboronic acid (185909-51-7) + (2Z,8E)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic acid ethyl ester (185909-50-6) → (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester (185909-52-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; In tetrahydrofuran; water; for 2h;

DOI:10.1016/S0040-4039(96)02110-7

Reference yield:

(S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyraldehyde (185909-45-9) → (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester (185909-52-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / Ti(OiPr)4, (S)-BINOL / CH₂Cl₂ / 144 h / -20 °C

2: 96 percent / NaH / dimethylformamide

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C

4: 75 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran / -78 °C

5: Et₃N-HF / acetonitrile

6: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 °C

7: 78 percent / CrCl₂ / dioxane; tetrahydrofuran

8: 83 percent / Pd(PPh₃)4, TlOH / tetrahydrofuran; H₂O / 2 h

With chromium dichloride; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; oxalyl dichloride; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium hexamethylsilazane; sodium hydride; ozone; dimethyl sulfoxide; triethylamine hydrofluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(96)02110-7

Reference yield:

(S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butan-1-ol → (2Z,8E,10E)-(5S,7S)-12-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester (185909-52-8)

Guidance literature:

Multi-step reaction with 9 steps

1: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 79 percent / Ti(OiPr)4, (S)-BINOL / CH₂Cl₂ / 144 h / -20 °C

3: 96 percent / NaH / dimethylformamide

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C

5: 75 percent / KN(TMS)2, 18-crown-6 / tetrahydrofuran / -78 °C

6: Et₃N-HF / acetonitrile

7: DMSO, (COCl)2, Et₃N / CH₂Cl₂ / -78 °C

8: 78 percent / CrCl₂ / dioxane; tetrahydrofuran

9: 83 percent / Pd(PPh₃)4, TlOH / tetrahydrofuran; H₂O / 2 h

With chromium dichloride; titanium(IV) isopropylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; TlOH; oxalyl dichloride; 18-crown-6 ether; (S)-[1,1']-binaphthalenyl-2,2'-diol; potassium hexamethylsilazane; sodium hydride; ozone; dimethyl sulfoxide; triethylamine hydrofluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(96)02110-7

upstream raw materials:

(E)-3-hydroxyprop-1-enylboronic acid

(2Z,8E)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic acid ethyl ester

(S)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyraldehyde

tert-Butyl-[(2S,4S)-4-methoxy-2-(4-methoxy-benzyloxy)-hept-6-enyloxy]-dimethyl-silane

Downstream raw materials:

(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trien-1-ol

(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienal

(2Z,8E,10E)-(5S,7S)-12-(tert-Butyl-dimethyl-silanyloxy)-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester

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