(E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

Base Information

• Chemical Name: (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester
• CAS No.: 209260-19-5
• Molecular Formula: C₃₈H₅₄O₅Si
• Molecular Weight: 618.929
• Mol file: 209260-19-5.mol

Synonyms:(E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

Chemical Property of (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

There total 12 articles about (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-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: 60.0%

(S)-2-methyl-hept-6-enal (184917-63-3) + (E)-4,4-Dimethyl-5-oxo-hept-2-enoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (209260-18-4) → (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (209260-19-5) + (E)-(6S,7R,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (209260-20-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 0.5 h, 2.) -78 deg C, 0.5 h;

Reference yield:

tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane (106731-74-2,119944-29-5,107033-46-5) → (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (209260-19-5)

Guidance literature:

Multi-step reaction with 3 steps

2: 86 percent / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h

3: 1) LDA / 1) THF, -78 deg C, 15 min, -40 deg c, 45 min, 2) THF, -40 deg C, 30 min

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja971109i

Reference yield:

(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}pent-4-en-2-ol (127793-64-0) → (E)-(6R,7S,8S)-7-Hydroxy-4,4,6,8-tetramethyl-5-oxo-trideca-2,12-dienoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester (209260-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 4-(dimethylamino)pyridine, 1-ethyl-3-((dimethylamino)propyl)carbodiimide hydrochloride / CH₂Cl₂ / 1) 0 deg C, 2 h, 2) 25 deg C, 12 h

2: 1) LDA / 1) THF, -78 deg C, 15 min, -40 deg c, 45 min, 2) THF, -40 deg C, 30 min

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja971109i

upstream raw materials:

(S)-2-methyl-hept-6-enal

(E)-4,4-Dimethyl-5-oxo-hept-2-enoic acid (S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-but-3-enyl ester

1-iodo-4-pentene

(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}pent-4-en-2-ol

Downstream raw materials:

(3E,13E)-(7R,8S,9S,16S)-16-(tert-Butyl-diphenyl-silanyloxymethyl)-8-hydroxy-5,5,7,9-tetramethyl-oxacyclohexadeca-3,13-diene-2,6-dione