(5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester

Base Information

• Chemical Name: (5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester
• CAS No.: 85442-91-7
• Molecular Formula: C₁₄H₂₄O₄Si
• Molecular Weight: 284.428
• Mol file: 85442-91-7.mol

Synonyms:(5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester

Chemical Property of (5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester

There total 1 articles about (5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic 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: 82.0%

(1R,2R,6R)-2-Triethylsilanyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester (85442-90-6) → (5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester (85442-91-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; diethyl ether; Ambient temperature;

DOI:10.1021/ja00348a070

Reference yield:

dimethyl diazomalonate (6773-29-1) + (5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester (85442-91-7) → 2-((1R,6R)-5-Methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester (85442-92-8)

Guidance literature:

With rhodium(II) acetate; In benzene; at 60 ℃; Yield given;

DOI:10.1021/ja00348a070

Reference yield:

(5R,6R)-5-Hydroxy-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester (85442-91-7) → (5S,6S)-5-(1-Carboxy-vinyloxy)-6-hydroxy-cyclohexa-1,3-dienecarboxylic acid (22642-82-6,85506-20-3)

Guidance literature:

Multi-step reaction with 5 steps

1: rhodium acetate / benzene / 60 °C

2: 1.) (C₂H₅)3N / 1.) CH₂Cl₂

3: 50 percent / aq. NaOH / methanol / 0 °C

4: 79 percent / HOAc / tetrahydrofuran; H₂O / 14 h / 0 °C

5: 23 percent / aq. NaOH / methanol / 0 °C

With rhodium(II) acetate; sodium hydroxide; acetic acid; triethylamine; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1021/ja00348a070

upstream raw materials:

(1R,2R,6R)-2-Triethylsilanyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester

Downstream raw materials:

2-((1R,6R)-5-Methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester

(5S,6S)-5-(1-Carboxy-vinyloxy)-6-hydroxy-cyclohexa-1,3-dienecarboxylic acid

dimethyl isochrismate

(5S,6S)-5-(1-Methoxycarbonyl-vinyloxy)-6-triethylsilanyloxy-cyclohexa-1,3-dienecarboxylic acid methyl ester