(S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one

Base Information

• Chemical Name: (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one
• CAS No.: 696642-13-4
• Molecular Formula: C₅₉H₉₄O₁₁Si
• Molecular Weight: 1007.47
• Mol file: 696642-13-4.mol

Synonyms:(S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one

Chemical Property of (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one

There total 8 articles about (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one 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: 44.0%

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal (198541-55-8) + [4-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-butyl]-triphenyl-phosphonium; iodide → (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one (696642-13-4)

Guidance literature:

[4-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-butyl]-triphenyl-phosphonium; iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jo049955g

Reference yield:

(R)-1-[(2R,5R)-5-((R)-1-Methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-prop-2-en-1-ol (608532-12-3) → (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one (696642-13-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / [(benzylidene)(PCy₃)(1,3-dimesitylimidazolidin-2-yl)RuCl₂] / CH₂Cl₂ / 36 h / 20 °C

2.1: 778.8 mg / hydrogen / Pd/C / ethyl acetate / 18 h / 20 °C

3.1: 29 mg / K₂CO₃; methanol / 18 h / 20 °C

4.1: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

5.1: 95 percent Turnov_. / sodium methoxide / methanol / 12 h / Heating

6.1: 88 percent / triphenylphosphine; imidazole; iodine / benzene / 2 h / Heating

7.1: 90 percent / N,N-diisopropylethylamine / toluene; acetonitrile / 24 h / Heating

8.1: BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

8.2: 44 percent / hexane; tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; methanol; n-butyllithium; hydrogen; iodine; sodium methylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene; 8.2: Wittig reaction;

DOI:10.1021/jo049955g

Reference yield:

2,2-Dimethyl-propionic acid 4-((2R,5S)-5-{(Z)-(1S,4R)-1-acetoxy-4-hydroxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-but-2-enyl}-tetrahydro-furan-2-yl)-butyl ester (608532-16-7) → (S)-3-[(E)-(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-non-5-enyl]-5-methyl-5H-furan-2-one (696642-13-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 778.8 mg / hydrogen / Pd/C / ethyl acetate / 18 h / 20 °C

2.1: 29 mg / K₂CO₃; methanol / 18 h / 20 °C

3.1: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

4.1: 95 percent Turnov_. / sodium methoxide / methanol / 12 h / Heating

5.1: 88 percent / triphenylphosphine; imidazole; iodine / benzene / 2 h / Heating

6.1: 90 percent / N,N-diisopropylethylamine / toluene; acetonitrile / 24 h / Heating

7.1: BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

7.2: 44 percent / hexane; tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; methanol; n-butyllithium; hydrogen; iodine; sodium methylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene; 7.2: Wittig reaction;

DOI:10.1021/jo049955g

upstream raw materials:

(R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-pentanal

(R)-1-[(2R,5R)-5-((R)-1-Methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-prop-2-en-1-ol

4-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-butan-1-ol

2,2-Dimethyl-propionic acid 4-((2R,5S)-5-{(Z)-(1S,4R)-1-acetoxy-4-hydroxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-but-2-enyl}-tetrahydro-furan-2-yl)-butyl ester

Downstream raw materials:

bullatanocin

(S)-3-[(R)-9-((2R,5S)-5-{(1S,4R)-1,4-Bis-methoxymethoxy-4-[(2R,5R)-5-((R)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-butyl}-tetrahydro-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-nonyl]-5-methyl-5H-furan-2-one