2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester

Base Information

• Chemical Name: 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester
• CAS No.: 790697-96-0
• Molecular Formula: C₃₄H₄₂O₅Si
• Molecular Weight: 558.79

Synonyms:2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester

Chemical Property of 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester

There total 4 articles about 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-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:

(S)-4-Bromo-2-(4-methoxy-benzyloxy)-pent-4-en-1-ol (790698-12-3) → 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester (790697-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

2.2: 82 percent / tetrahydrofuran; pentane / 3 h / 20 °C

3.1: PPh₃ / tetrahydrofuran / 0.17 h / 20 °C

3.2: 87 percent / DEAD / tetrahydrofuran / 2 h

With 1H-imidazole; tert.-butyl lithium; triphenylphosphine; In tetrahydrofuran; dichloromethane; pentane; 3.1: Mitsunobu reaction;

DOI:10.1021/ja0455852

Reference yield:

(R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone → 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester (790697-96-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

1.2: 71 percent / tetrahydrofuran / -78 - -45 °C

2.1: sodium borohydride / tetrahydrofuran / 1 h / 20 °C

2.2: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C

3.1: 72 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

4.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

4.2: 82 percent / tetrahydrofuran; pentane / 3 h / 20 °C

5.1: PPh₃ / tetrahydrofuran / 0.17 h / 20 °C

5.2: 87 percent / DEAD / tetrahydrofuran / 2 h

With 1H-imidazole; sodium tetrahydroborate; tert.-butyl lithium; sodium hexamethyldisilazane; triphenylphosphine; In tetrahydrofuran; dichloromethane; pentane; 5.1: Mitsunobu reaction;

DOI:10.1021/ja0455852

Reference yield:

3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one (790697-94-8) → 2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(S)-(4-methoxy-benzyloxy)-propyl]acrylic acid 1-(S)-methyl-allyl ester (790697-96-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium borohydride / tetrahydrofuran / 1 h / 20 °C

1.2: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C

2.1: 72 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

3.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

3.2: 82 percent / tetrahydrofuran; pentane / 3 h / 20 °C

4.1: PPh₃ / tetrahydrofuran / 0.17 h / 20 °C

4.2: 87 percent / DEAD / tetrahydrofuran / 2 h

With 1H-imidazole; sodium tetrahydroborate; tert.-butyl lithium; triphenylphosphine; In tetrahydrofuran; dichloromethane; pentane; 4.1: Mitsunobu reaction;

DOI:10.1021/ja0455852

upstream raw materials:

(S)-4-Bromo-2-(4-methoxy-benzyloxy)-pent-4-en-1-ol

3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one

(R)-[4-bromo-2-(4-methoxy-benzyloxy)-pent-4-enyloxy]-tert-butyl-diphenyl-silane

Downstream raw materials:

(S)-3-[(R)-7-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(4-methoxy-benzyloxy)-heptyl]-5-methyl-5H-furan-2-one

3-[7-(5-(S)-{1-(S),4-(R)-bis-methoxymethoxy-4-[5-(R)-(1-(R)-methoxymethoxy-tridecyl)tetrahydrofuran-2-(R)-yl]butyl}tetrahydrofuran-2-(S)-yl)-2-(R)-(4-methoxybenzyloxy)hept-3-en-5-ynyl]-5-(S)-methyl-5H-furan-2-one

3-[4-iodo-2-(4-methoxy-benzyloxy)but-3-enyl]-5-methyl-5H-furan-2-one

3-[3-hydroxy-2-(4-methoxy-benzyloxy)propyl]-5-methyl-5H-furan-2-one

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