2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester

Base Information

• Chemical Name: 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester
• CAS No.: 314273-48-8
• Molecular Formula: C₂₃H₃₈O₄Si
• Molecular Weight: 406.638
• Mol file: 314273-48-8.mol

Synonyms:2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester

Chemical Property of 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester

There total 5 articles about 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl 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:

methyl 2-bromomethylbenzoate (2417-73-4) + (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hept-6-yn-1-ol → 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester (314273-48-8)

Guidance literature:

(3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-hept-6-yn-1-ol; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 2h; Heating;

methyl 2-bromomethylbenzoate; With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(00)01420-9

Reference yield:

(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methyl-1-pentanol (188926-24-1) → 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester (314273-48-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine; DMAP / CH₂Cl₂ / 16 h / 20 °C

2.1: dimethylsulfoxide / 18 h / 20 °C

3.1: HF*pyridine; pyridine / tetrahydrofuran / 3 h / 20 °C

4.1: Bu₃SnH; AIBN / benzene / 2 h / Heating

4.2: Pd₂(dba)3; TFP / 1-methyl-pyrrolidin-2-one / 24 h / 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridine hydrogenfluoride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene; 4.2: Still coupling;

DOI:10.1016/S0040-4039(00)01420-9

Reference yield:

(3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene (219606-81-2) → 2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid methyl ester (314273-48-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: O₃ / methanol; CH₂Cl₂ / -78 °C

1.2: NaBH₄ / CH₂Cl₂; methanol / 0.33 h

2.1: pyridine; DMAP / CH₂Cl₂ / 16 h / 20 °C

3.1: dimethylsulfoxide / 18 h / 20 °C

4.1: HF*pyridine; pyridine / tetrahydrofuran / 3 h / 20 °C

5.1: Bu₃SnH; AIBN / benzene / 2 h / Heating

5.2: Pd₂(dba)3; TFP / 1-methyl-pyrrolidin-2-one / 24 h / 20 °C

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridine hydrogenfluoride; ozone; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; benzene; 5.2: Still coupling;

DOI:10.1016/S0040-4039(00)01420-9

upstream raw materials:

methyl 2-bromomethylbenzoate

(2R,3S)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-2-methyl-1-pentanol

(3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene

(4R,5S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hept-1-yne

Downstream raw materials:

2-[(E)-(5R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-5-methyl-oct-2-enyl]-benzoic acid