acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester

Base Information

• Chemical Name: acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester
• CAS No.: 887602-21-3
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44
• Mol file: 887602-21-3.mol

Synonyms:acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester

Chemical Property of acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester

There total 6 articles about acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl 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:

(E)-(2S,3S,4S)-1-(4-Methoxy-benzyloxy)-2,4-dimethyl-hept-5-en-3-ol (887602-36-0) + acryloyl chloride (814-68-6,25189-84-8) → acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester (887602-21-3)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ja0609708

Reference yield:

(2S,3S)-3-(Diisopropyl-prop-1-ynyl-silanyloxy)-2-methyl-pent-4-en-1-ol (887602-35-9) → acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester (887602-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / CSA / CH₂Cl₂ / -10 - 20 °C

2: 65 percent / Ti(i-PrO)3Cl; i-PrMgCl / diethyl ether / 6 h

3: TBAF*H₂O / dimethylformamide / 6 h / 75 °C

4: 0.131 g / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0 - 20 °C

With triisopropoxytitanium(IV) chloride; dmap; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0609708

Reference yield:

(4R,2'R,3'S)-4-benzyl-3-[3-hydroxy-2-methylpent-4-enoyl]-oxazolidin-2-one (321921-73-7) → acrylic acid 1-[2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-pent-3-enyl ester (887602-21-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / imidazole / dimethylformamide / 1 h / 20 °C

2: 78 percent / LiBH₄ / tetrahydrofuran / 6 h / 0 °C

3: 82 percent / CSA / CH₂Cl₂ / -10 - 20 °C

4: 65 percent / Ti(i-PrO)3Cl; i-PrMgCl / diethyl ether / 6 h

5: TBAF*H₂O / dimethylformamide / 6 h / 75 °C

6: 0.131 g / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; triisopropoxytitanium(IV) chloride; dmap; lithium borohydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja0609708

upstream raw materials:

(E)-(2S,3S,4S)-1-(4-Methoxy-benzyloxy)-2,4-dimethyl-hept-5-en-3-ol

acryloyl chloride

(2S,3S)-3-(Diisopropyl-prop-1-ynyl-silanyloxy)-2-methyl-pent-4-en-1-ol

(4R,2'R,3'S)-4-benzyl-3-[3-hydroxy-2-methylpent-4-enoyl]-oxazolidin-2-one

Downstream raw materials:

(+)-(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienal

(+)-(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dien-1-ol

(3Z,16Z,22E)-(5S,6S,7R,11S,13S,14R,15S,18S,20S,21R)-14,18,20,24-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,16,22-tetraen-8-one

14,18,20,24-tetrakis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,11,13,15,21-hexamethyl-tetracosa-1,3,9,16,22-pentaen-8-one