(S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate

Base Information

• Chemical Name: (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate
• CAS No.: 1434059-34-3
• Molecular Formula: C₃₄H₅₈O₅Si
• Molecular Weight: 574.917
• Mol file: 1434059-34-3.mol

Synonyms:(S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate

Chemical Property of (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate

There total 17 articles about (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate 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: 82.0%

(3S)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-4-pentenoicacid (1039357-61-3) + (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol (1434059-33-2) → (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate (1434059-34-3)

Guidance literature:

(3S)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}-4-pentenoicacid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

(3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol; With dmap; In toluene; at 0 ℃; for 0.25h; Inert atmosphere;

DOI:10.1039/c3ob27518c

Reference yield:

(R)-tert-butyl(5-(4-methoxybenzyloxy)hept-6-enyloxy)diphenylsilane (1434059-29-6) → (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate (1434059-34-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

3.1: L-proline / chloroform / 2 h / 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate / ethanol / 2 h / 0 °C / Inert atmosphere

5.1: acetic acid; zinc / 12 h / 20 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.67 h / 20 °C / Inert atmosphere

6.2: 1 h / 0 - 20 °C / Inert atmosphere

7.1: dilithium tetrachlorocuprate / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

8.2: 0.25 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; dilithium tetrachlorocuprate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; L-proline; zinc; In tetrahydrofuran; ethanol; dichloromethane; chloroform; mineral oil;

DOI:10.1039/c3ob27518c

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-(tertbutyldimethylsilyloxy)pent-4-enoate (1434059-34-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: scandium tris(trifluoromethanesulfonate) / toluene / 0.25 h / -20 - -10 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: L-proline / chloroform / 2 h / 0 °C / Inert atmosphere

5.1: sodium tetrahydroborate / ethanol / 2 h / 0 °C / Inert atmosphere

6.1: acetic acid; zinc / 12 h / 20 °C / Inert atmosphere

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.67 h / 20 °C / Inert atmosphere

7.2: 1 h / 0 - 20 °C / Inert atmosphere

8.1: dilithium tetrachlorocuprate / tetrahydrofuran / -78 - 20 °C / Inert atmosphere

8.2: Inert atmosphere

9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

9.2: 0.25 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; dilithium tetrachlorocuprate; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; L-proline; scandium tris(trifluoromethanesulfonate); zinc; In tetrahydrofuran; ethanol; dichloromethane; chloroform; toluene; mineral oil;

DOI:10.1039/c3ob27518c

upstream raw materials:

(R)-tert-butyl(5-(4-methoxybenzyloxy)hept-6-enyloxy)diphenylsilane

O-(4-methoxybenzyl)-trichloroacetimidate

(R)-5-(4-methoxybenzyloxy)hept-6-en-1-ol

(R)-5-(4-methoxybenzyloxy)hept-6-enal

Downstream raw materials:

(S)-((3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-yl) 3-hydroxypent-4-enoate