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

Base Information

• Chemical Name: 2-((1R,6R)-5-Methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester
• CAS No.: 85442-92-8
• Molecular Formula: C₁₉H₃₀O₈Si
• Molecular Weight: 414.528
• Mol file: 85442-92-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 2-((1R,6R)-5-Methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl 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:

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:

(1R,2R,6R)-2-Triethylsilanyloxy-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester (85442-90-6) → 2-((1R,6R)-5-Methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester (85442-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / diethyl ether; methanol / Ambient temperature

2: rhodium acetate / benzene / 60 °C

With rhodium(II) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; diethyl ether; benzene;

DOI:10.1021/ja00348a070

Reference yield:

2-((1R,6R)-5-Methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester (85442-92-8) → (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 4 steps

1: 1.) (C₂H₅)3N / 1.) CH₂Cl₂

2: 50 percent / aq. NaOH / methanol / 0 °C

3: 79 percent / HOAc / tetrahydrofuran; H₂O / 14 h / 0 °C

4: 23 percent / aq. NaOH / methanol / 0 °C

With sodium hydroxide; acetic acid; triethylamine; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00348a070

upstream raw materials:

dimethyl diazomalonate

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

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

Downstream raw materials:

[2,2-Bis-methoxycarbonyl-2-((1R,6R)-5-methoxycarbonyl-6-triethylsilanyloxy-cyclohexa-2,4-dienyloxy)-ethyl]-trimethyl-ammonium; iodide

(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