(2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester

Base Information

• Chemical Name: (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester
• CAS No.: 192520-06-2
• Molecular Formula: C₂₄H₃₄O₆SSi
• Molecular Weight: 478.682
• Mol file: 192520-06-2.mol

Synonyms:(2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester

Chemical Property of (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester

There total 6 articles about (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl 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: 46.0%

t-butyldimethylsiyl triflate (69739-34-0) + (E)-5-(4-Methoxy-phenylsulfanyl)-2-methyl-3-oxo-pent-4-enoic acid (E)-3-methoxycarbonyl-allyl ester (192520-16-4) → (2Z,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester + (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester (192520-06-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 72h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(97)00606-6

Reference yield:

(E)-3-(4-Methoxy-phenylsulfanyl)-prop-2-en-1-ol → (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester (192520-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: iodobenzoic acid / dimethylsulfoxide; tetrahydrofuran / 0.5 h / 20 °C

2: 67 percent / Zn / tetrahydrofuran / 1 h / 55 °C / Irradiation

3: 66 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 46 percent / Et₃N / CH₂Cl₂ / 72 h / 20 °C

With pyridine; 2-Iodobenzoic acid; Dess-Martin periodane; triethylamine; zinc; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(97)00606-6

Reference yield:

methyl 4-hydroxy-2-butenoate (29576-13-4) → (2E,4E)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenylsulfanyl)-2-methyl-penta-2,4-dienoic acid (E)-3-methoxycarbonyl-allyl ester (192520-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / pyridine / CH₂Cl₂ / 0.17 h / 20 °C

2: 67 percent / Zn / tetrahydrofuran / 1 h / 55 °C / Irradiation

3: 66 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 46 percent / Et₃N / CH₂Cl₂ / 72 h / 20 °C

With pyridine; Dess-Martin periodane; triethylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(97)00606-6

upstream raw materials:

t-butyldimethylsiyl triflate

(E)-5-(4-Methoxy-phenylsulfanyl)-2-methyl-3-oxo-pent-4-enoic acid (E)-3-methoxycarbonyl-allyl ester

methyl 4-hydroxy-2-butenoate

(E)-4-(2-Bromo-propionyloxy)-but-2-enoic acid methyl ester