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

Base Information

• Chemical Name: (2Z,8E)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic acid ethyl ester
• CAS No.: 185909-50-6
• Molecular Formula: C₂₁H₂₉IO₅
• Molecular Weight: 488.363

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (2Z,8E)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic 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: 78.0%

iodoform (75-47-8) + (Z)-(5S,7S)-5-Methoxy-7-(4-methoxy-benzyloxy)-2-methyl-8-oxo-oct-2-enoic acid ethyl ester (185909-49-3) → (2Z,8E)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic acid ethyl ester (185909-50-6)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; 1,4-dioxane;

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)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic acid ethyl ester (185909-50-6)

Guidance literature:

Multi-step reaction with 7 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

With chromium dichloride; titanium(IV) isopropylate; 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; 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)-(5S,7S)-9-Iodo-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-nona-2,8-dienoic acid ethyl ester (185909-50-6)

Guidance literature:

Multi-step reaction with 8 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

With chromium dichloride; titanium(IV) isopropylate; 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; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

iodoform

(Z)-(5S,7S)-5-Methoxy-7-(4-methoxy-benzyloxy)-2-methyl-8-oxo-oct-2-enoic 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-Hydroxy-5-methoxy-7-(4-methoxy-benzyloxy)-2-methyl-dodeca-2,8,10-trienoic acid ethyl ester

(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

(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

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