(Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester

Base Information

• Chemical Name: (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester
• CAS No.: 213328-39-3
• Molecular Formula: C₄₃H₆₀O₆Si₂
• Molecular Weight: 729.117

Synonyms:

Chemical Property of (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester

There total 10 articles about (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl 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:

benzoic acid 6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-2-oxo-hex-4-ynyl ester → (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester (213328-39-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 88 percent / AgNO₃ / acetone / 1 h / Heating

3.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / -78 - 20 °C

4.1: 94 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 0 °C

5.1: 18-crown-6; potassium bis(trimethylsilyl)amide / hexane; tetrahydrofuran / 0.67 h / -78 °C

5.2: 88 percent / hexane; tetrahydrofuran / 0.5 h / -78 °C

6.1: 95 percent / K₂CO₃ / methanol / 3 h / 20 °C

7.1: 83 percent / MnO₂ / CH₂Cl₂ / 6 h

8.1: (R,R)-mono-O-(2,6-dimethoxybenzoyl)tartaric acid; BH₃*THF; trifluoroacetic anhydride / acetonitrile / 15 h / -78 °C

9.1: Hunig's base / CH₂Cl₂ / -78 - 20 °C

With manganese(IV) oxide; borane-THF; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; -2-<(2,6-dimethoxybenzoyl)oxy>-3-hydroxybutanedioic acid; trifluoroacetic anhydride; silver nitrate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; acetonitrile; 1.1: Isomerization / 2.1: Cyclization / 3.1: desilylation / 4.1: Oxidation / 5.1: Metallation / 5.2: Still-Horner-Emmons reaction / 6.1: deacylation / 7.1: Oxidation / 8.1: Addition / 9.1: Etherification;

DOI:10.1021/jo980603h

Reference yield:

benzoic acid 6-(tert-butyl-diphenyl-silanyloxy)-3-methyl-2-oxo-hexa-3,4-dienyl ester (213327-94-7) → (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester (213328-39-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / AgNO₃ / acetone / 1 h / Heating

2.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / -78 - 20 °C

3.1: 94 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 0 °C

4.1: 18-crown-6; potassium bis(trimethylsilyl)amide / hexane; tetrahydrofuran / 0.67 h / -78 °C

4.2: 88 percent / hexane; tetrahydrofuran / 0.5 h / -78 °C

5.1: 95 percent / K₂CO₃ / methanol / 3 h / 20 °C

6.1: 83 percent / MnO₂ / CH₂Cl₂ / 6 h

7.1: (R,R)-mono-O-(2,6-dimethoxybenzoyl)tartaric acid; BH₃*THF; trifluoroacetic anhydride / acetonitrile / 15 h / -78 °C

8.1: Hunig's base / CH₂Cl₂ / -78 - 20 °C

With manganese(IV) oxide; borane-THF; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; -2-<(2,6-dimethoxybenzoyl)oxy>-3-hydroxybutanedioic acid; trifluoroacetic anhydride; silver nitrate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; acetonitrile; 1.1: Cyclization / 2.1: desilylation / 3.1: Oxidation / 4.1: Metallation / 4.2: Still-Horner-Emmons reaction / 5.1: deacylation / 6.1: Oxidation / 7.1: Addition / 8.1: Etherification;

DOI:10.1021/jo980603h

Reference yield:

6-[(tert-butyldiphenylsilyl)oxy]-3-methyl-1-(benzoyloxy)-4-hexyn-2-ol (213327-93-6) → (Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-2-isopropenyl-1-(2-trimethylsilanyl-ethoxymethoxy)-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester (213328-39-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 90 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 1 h

2.1: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 88 percent / AgNO₃ / acetone / 1 h / Heating

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / -78 - 20 °C

5.1: 94 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 0 °C

6.1: 18-crown-6; potassium bis(trimethylsilyl)amide / hexane; tetrahydrofuran / 0.67 h / -78 °C

6.2: 88 percent / hexane; tetrahydrofuran / 0.5 h / -78 °C

7.1: 95 percent / K₂CO₃ / methanol / 3 h / 20 °C

8.1: 83 percent / MnO₂ / CH₂Cl₂ / 6 h

9.1: (R,R)-mono-O-(2,6-dimethoxybenzoyl)tartaric acid; BH₃*THF; trifluoroacetic anhydride / acetonitrile / 15 h / -78 °C

10.1: Hunig's base / CH₂Cl₂ / -78 - 20 °C

With manganese(IV) oxide; borane-THF; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; -2-<(2,6-dimethoxybenzoyl)oxy>-3-hydroxybutanedioic acid; trifluoroacetic anhydride; silver nitrate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone; acetonitrile; 1.1: Oxidation / 2.1: Isomerization / 3.1: Cyclization / 4.1: desilylation / 5.1: Oxidation / 6.1: Metallation / 6.2: Still-Horner-Emmons reaction / 7.1: deacylation / 8.1: Oxidation / 9.1: Addition / 10.1: Etherification;

DOI:10.1021/jo980603h

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

(Z)-3-{5-[(1R,2S)-7-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-2-isopropenyl-hept-5-ynyl]-4-methyl-furan-2-yl}-2-methyl-acrylic acid ethyl ester

(Z)-3-(5-Formyl-4-methyl-furan-2-yl)-2-methyl-acrylic acid ethyl ester

benzoic acid 5-formyl-3-methyl-furan-2-ylmethyl ester

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