(E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester
• CAS No.: 183504-74-7
• Molecular Formula: C₃₁H₃₇ClO₃Si
• Molecular Weight: 521.171
• Mol file: 183504-74-7.mol

Synonyms:(E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester

Chemical Property of (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester

There total 5 articles about (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (E)-(R)-5-(4-Chloro-phenyl)-7-hydroxy-hept-2-enoic acid ethyl ester (183504-78-1) → (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester (183504-74-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 15h; Ambient temperature;

DOI:10.1021/jo961096b

Reference yield:

diethyl 3-(4-chlorophenyl)glutarate (101104-10-3) → (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester (183504-74-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / α-chymotrypsin, aq. KCl / 120 h / Ambient temperature; pH 7.8

2: LiBH₄ / 1,2-dimethoxy-ethane; methanol / 1 h / Heating

3: p-toluenesulfonic acid / toluene / 3.5 h / Heating

4: 1.) n-BuLi, 3.) DIBALH / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 10 min; 3) THF, hexane, toluene, rt, overnight

5: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

With dmap; lithium borohydride; n-butyllithium; potassium chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; α-chymotrypsin; In methanol; 1,2-dimethoxyethane; dichloromethane; toluene;

DOI:10.1021/jo961096b

Reference yield:

(S)-3-(4-Chloro-phenyl)-5-hydroxy-pentanoic acid → (E)-(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-hept-2-enoic acid ethyl ester (183504-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid / toluene / 3.5 h / Heating

2: 1.) n-BuLi, 3.) DIBALH / 1) THF, hexane, -78 deg C, 30 min; 2) THF, hexane, -78 deg C, 10 min; 3) THF, hexane, toluene, rt, overnight

3: 100 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

With dmap; n-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; In dichloromethane; toluene;

DOI:10.1021/jo961096b

upstream raw materials:

tert-butylchlorodiphenylsilane

(E)-(R)-5-(4-Chloro-phenyl)-7-hydroxy-hept-2-enoic acid ethyl ester

diethyl 3-(4-chlorophenyl)glutarate

4-(4-chlorophenyl)tetrahydro-2H-pyran-2-one

Downstream raw materials:

(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-heptanoyl chloride

3-[5-bromo-3-(4-chlorophenyl)pentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

(3R,4S)-3-[3-(4-chlorophenyl)-5-hydroxypentyl]-4-(4-methoxyphenyl)-1-phenyl-2-azetidinone

(R)-7-(tert-Butyl-diphenyl-silanyloxy)-5-(4-chloro-phenyl)-heptanoic acid methyl ester