(S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester

Base Information

• Chemical Name: (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester
• CAS No.: 401911-90-8
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 401911-90-8.mol

Synonyms:

Chemical Property of (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester

There total 4 articles about (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-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:

(S)-2-methoxy-2-phenylacetic acid (26164-26-1) → (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester (401911-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: [R-(R*,R*)]-(+)-bis(α-methylbenzyl)amidolithium; tert-butyldimethylsilyl chloride / tetrahydrofuran; hexamethylphosphoric acid triamide / 24 h / -78 °C

1.2: lithium perchlorate*diethyl ether; DIBALH / toluene / 0 - 20 °C

1.3: 83 percent / DCC; DMAP / CH₂Cl₂ / 0 °C

2.1: LiAl(O-t-Bu)3H / tetrahydrofuran / -78 °C

3.1: 2,6-di-tert-butylpyridine

With 2,6-di-tert-butyl-pyridine; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; tert-butyldimethylsilyl chloride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ol010253c

Reference yield:

(1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one (37081-58-6) → (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester (401911-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: [R-(R*,R*)]-(+)-bis(α-methylbenzyl)amidolithium; tert-butyldimethylsilyl chloride / tetrahydrofuran; hexamethylphosphoric acid triamide / 24 h / -78 °C

1.2: lithium perchlorate*diethyl ether; DIBALH / toluene / 0 - 20 °C

1.3: 83 percent / DCC; DMAP / CH₂Cl₂ / 0 °C

2.1: LiAl(O-t-Bu)3H / tetrahydrofuran / -78 °C

3.1: 2,6-di-tert-butylpyridine

With 2,6-di-tert-butyl-pyridine; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; tert-butyldimethylsilyl chloride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ol010253c

Reference yield:

(S)-Methoxy-phenyl-acetic acid (1R,5R,7S)-5,7-dimethyl-6-oxo-cyclohept-2-enyl ester (401911-88-4) → (S)-Methoxy-phenyl-acetic acid (1R,5R,6R,7R)-6-methoxy-5,7-dimethyl-cyclohept-2-enyl ester (401911-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAl(O-t-Bu)3H / tetrahydrofuran / -78 °C

2: 2,6-di-tert-butylpyridine

With 2,6-di-tert-butyl-pyridine; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran;

DOI:10.1021/ol010253c

upstream raw materials:

methyl trifluoromethanesulfonate

(S)-2-methoxy-2-phenylacetic acid

(1R,2S,4R,5S)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-en-3-one

(S)-Methoxy-phenyl-acetic acid (1R,5R,7S)-5,7-dimethyl-6-oxo-cyclohept-2-enyl ester