(1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate

Base Information

• Chemical Name: (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate
• CAS No.: 304859-79-8
• Molecular Formula: C₃₃H₄₅BrO₅
• Molecular Weight: 601.621
• Mol file: 304859-79-8.mol

Synonyms:(1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate

Chemical Property of (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate

There total 24 articles about (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate 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: 87.0%

(1'S)-2-methoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)phenol (222022-88-0) + 2-Bromo-3,4-dimethoxy-5-((S)-1,2,2-trimethyl-cyclopentyl)-benzoyl chloride → (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate (304859-79-8)

Guidance literature:

(1'S)-2-methoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)phenol; With sodium hydride; In tetrahydrofuran; for 0.5h;

2-Bromo-3,4-dimethoxy-5-((S)-1,2,2-trimethyl-cyclopentyl)-benzoyl chloride; In tetrahydrofuran; dichloromethane; Further stages.;

DOI:10.1021/ja001455r

Reference yield:

4-hydroxy-3-iodo-5-methoxybenzyl alcohol (37987-21-6) → (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate (304859-79-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: (CBrCl₂)2; PPh₃ / CH₂Cl₂ / 0 - 20 °C

2.1: 3.60 g / LiAlH₄ / CH₂Cl₂; diethyl ether / 2.5 h / 20 °C

3.1: 79 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 24.5 h / 20 °C

4.1: PPh₃; NaOAc / Pd(OAc)2 / dimethylformamide / 120 °C

4.2: 72 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

5.1: BH₃*THF; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza...

6.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

7.1: 98 percent / K₂CO₃ / acetone / 48 h

8.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -60 °C

8.2: 98 percent / Et₃N / CH₂Cl₂ / 2 h / -60 - 20 °C

9.1: NH₂NH₂*H₂O / bis-(2-hydroxy-ethyl) ether / 4 h / 160 °C

9.2: 91 percent / NaOH / bis-(2-hydroxy-ethyl) ether / 6 h / 180 °C

10.1: 90 percent / BBr₃ / CH₂Cl₂ / 3 h / 0 °C

11.1: 78 percent / K₂CO₃ / acetone / 48 h

12.1: 98 percent / Cs₂CO₃ / acetone / 48 h

13.1: H₂ / Pd/C / diethyl ether; ethyl acetate / 5 h / atmospheric pressure

14.1: NaH / tetrahydrofuran / 0.5 h

14.2: 87 percent / CH₂Cl₂; tetrahydrofuran

With dmap; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; 1,2-dibromo-1,1,2,2-tetrachloroethane; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza..; hydrogen; sodium acetate; boron tribromide; sodium hydride; potassium carbonate; caesium carbonate; hydrazine hydrate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; diethylene glycol; 4.1: Heck reaction / 5.1: Corey-Bakshi-Shibata reduction / 8.1: Swern oxidation / 8.2: Swern oxidation / 9.1: Wolff-Kishner reduction / 9.2: Wolff-Kishner reduction;

DOI:10.1021/ja001455r

Reference yield:

5-iodovaniline (5438-36-8) → (1''S,1'''S)-[2'-methoxy-5'-methyl-3'-(1''',2''',2'''-trimethylcyclopentyl)-phenyl] 2-bromo-3,4-dimethoxy-5-(1'',2'',2''-trimethylcyclopentyl)benzoate (304859-79-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: NaBH₄; NaOH / methanol / 0 - 20 °C

2.1: (CBrCl₂)2; PPh₃ / CH₂Cl₂ / 0 - 20 °C

3.1: 3.60 g / LiAlH₄ / CH₂Cl₂; diethyl ether / 2.5 h / 20 °C

4.1: 79 percent / dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 24.5 h / 20 °C

5.1: PPh₃; NaOAc / Pd(OAc)2 / dimethylformamide / 120 °C

5.2: 72 percent / H₂ / Pd/C / ethanol / 12 h / atmospheric pressure

6.1: BH₃*THF; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza...

7.1: 97 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

8.1: 98 percent / K₂CO₃ / acetone / 48 h

9.1: (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -60 °C

9.2: 98 percent / Et₃N / CH₂Cl₂ / 2 h / -60 - 20 °C

10.1: NH₂NH₂*H₂O / bis-(2-hydroxy-ethyl) ether / 4 h / 160 °C

10.2: 91 percent / NaOH / bis-(2-hydroxy-ethyl) ether / 6 h / 180 °C

11.1: 90 percent / BBr₃ / CH₂Cl₂ / 3 h / 0 °C

12.1: 78 percent / K₂CO₃ / acetone / 48 h

13.1: 98 percent / Cs₂CO₃ / acetone / 48 h

14.1: H₂ / Pd/C / diethyl ether; ethyl acetate / 5 h / atmospheric pressure

15.1: NaH / tetrahydrofuran / 0.5 h

15.2: 87 percent / CH₂Cl₂; tetrahydrofuran

With dmap; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; 1,2-dibromo-1,1,2,2-tetrachloroethane; (5S)-2-B-methyl-4,4-diphenyl-1,5-trimethylene[3.2.1]oxaza..; hydrogen; sodium acetate; boron tribromide; sodium hydride; potassium carbonate; caesium carbonate; hydrazine hydrate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; diethylene glycol; 5.1: Heck reaction / 6.1: Corey-Bakshi-Shibata reduction / 9.1: Swern oxidation / 9.2: Swern oxidation / 10.1: Wolff-Kishner reduction / 10.2: Wolff-Kishner reduction;

DOI:10.1021/ja001455r

upstream raw materials:

(1'S)-2-methoxy-5-methyl-3-(1',2',2'-trimethylcyclopentyl)phenol

(1R,2R)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentyl-1-carbaldehyde

(1R,2S)-2-(2',3'-dimethoxy-5'-methylphenyl)-1,2-dimethylcyclopentylmethyl alcohol

4-hydroxy-3-iodo-5-methoxybenzyl alcohol