(E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid

Base Information

• Chemical Name: (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid
• CAS No.: 851760-00-4
• Molecular Formula: C₂₃H₃₀O₄Si
• Molecular Weight: 398.574
• Mol file: 851760-00-4.mol

Synonyms:(E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid

Chemical Property of (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid

There total 3 articles about (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid 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:

(4-methoxybenzyloxy)-acetic acid (E)-(S)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl ester → (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid (851760-00-4)

Guidance literature:

(4-methoxybenzyloxy)-acetic acid (E)-(S)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ol0501875

Reference yield:

(E)-(S)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol (851759-97-2) → (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid (851760-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DCC; DMAP / toluene / 0 - 20 °C

2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: TMSCl / tetrahydrofuran / -78 - 20 °C

With dmap; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1021/ol0501875

Reference yield:

p-methoxybenzyloxy acetic acid (88920-24-5) → (E)-(2R,3R)-3-(dimethyl-phenyl-silanyl)-2-(4-methoxy-benzyloxy)-3-methyl-hex-4-enoic acid (851760-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DCC; DMAP / toluene / 0 - 20 °C

2.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

2.2: TMSCl / tetrahydrofuran / -78 - 20 °C

With dmap; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1021/ol0501875

upstream raw materials:

(E)-(S)-4-(dimethyl-phenyl-silanyl)-pent-3-en-2-ol

p-methoxybenzyloxy acetic acid

Downstream raw materials:

(2S,3S,4R,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

(4R,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(4S,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester

(2S,3R,4R,5R,6R)-4-hydroxy-3,5-dimethyl-6-(2,3,5,6-tetramethoxy-4-methyl-phenyl)-tetrahydro-pyran-2-carboxylic acid methyl ester