Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester
• CAS No.: 1026914-62-4
• Molecular Formula: C₅₀H₈₄O₁₂
• Molecular Weight: 877.21

Synonyms:

Chemical Property of Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester

There total 25 articles about Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl 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:

nonylmagnesium bromide (39691-62-8) → Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester (1026914-62-4)

Guidance literature:

Multi-step reaction with 8 steps

1: CuBr / tetrahydrofuran / 1 h / 0 °C

2: 64 percent / i-Pr₂NEt / tetrahydrofuran; CH₂Cl₂ / 24 h / Ambient temperature

3: 87 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: CrO₃, H₂SO₄ / acetone / 0.33 h / -20 °C

5: ethyl acetate / 0 °C

6: LDA / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 10 min

7: aq. CSA / methanol / 2 h / Ambient temperature

8: pyridine / 2 h

With pyridine; chromium(VI) oxide; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; copper(I) bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/jo00119a019

Reference yield:

(R)-13-(tert-Butyl-dimethyl-silanyloxy)-10-methoxymethoxy-tridecan-1-ol (165961-00-2) → Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester (1026914-62-4)

Guidance literature:

Multi-step reaction with 15 steps

1: 97 percent / pyridine / 41 h / -20 °C

2: 92 percent / NaH / tetrahydrofuran / 1.) 30 min, 2.) room temp., 2 h

3: 95 percent / aq. magnesium monoperoxyphthalate / ethanol / 12 h / Ambient temperature

4: 83 percent / n-BuLi / hexane; 1,2-dimethoxy-ethane / 0.17 h / Ambient temperature

5: 60 percent / sodium amalgam / ethanol / 24 h / Ambient temperature

6: 42 percent / pyridine / 48 h / -20 °C

7: 90 percent / aq. K₂CO₃ / ethanol / 0.17 h / Ambient temperature

8: CuBr / tetrahydrofuran / 1 h / 0 °C

9: 64 percent / i-Pr₂NEt / tetrahydrofuran; CH₂Cl₂ / 24 h / Ambient temperature

10: 87 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

11: CrO₃, H₂SO₄ / acetone / 0.33 h / -20 °C

12: ethyl acetate / 0 °C

13: LDA / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 10 min

14: aq. CSA / methanol / 2 h / Ambient temperature

15: pyridine / 2 h

With pyridine; chromium(VI) oxide; sodium amalgam; n-butyllithium; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; magnesium monoperoxyphthalate hexahydrate; N-ethyl-N,N-diisopropylamine; copper(I) bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/jo00119a019

Reference yield:

(-)-(2R,3R,6R,7R,10R,11S)-11,12-Dihydroxy-1,2:3,6:7,10-triepoxydodecane (165960-93-0) → Benzoic acid (S)-4-{(2R,13R)-2,13-bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-2-methyl-5-oxo-tetrahydro-furan-3-yl ester (1026914-62-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / n-BuLi / hexane; 1,2-dimethoxy-ethane / 0.17 h / Ambient temperature

2: 60 percent / sodium amalgam / ethanol / 24 h / Ambient temperature

3: 42 percent / pyridine / 48 h / -20 °C

4: 90 percent / aq. K₂CO₃ / ethanol / 0.17 h / Ambient temperature

5: CuBr / tetrahydrofuran / 1 h / 0 °C

6: 64 percent / i-Pr₂NEt / tetrahydrofuran; CH₂Cl₂ / 24 h / Ambient temperature

7: 87 percent / n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

8: CrO₃, H₂SO₄ / acetone / 0.33 h / -20 °C

9: ethyl acetate / 0 °C

10: LDA / hexane; tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 10 min

11: aq. CSA / methanol / 2 h / Ambient temperature

12: pyridine / 2 h

With pyridine; chromium(VI) oxide; sodium amalgam; n-butyllithium; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium carbonate; N-ethyl-N,N-diisopropylamine; copper(I) bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/jo00119a019

upstream raw materials:

benzoyl chloride

(S)-3-{(2R,13R)-2,13-Bis-methoxymethoxy-13-[(2R,5R,2'R,5'R)-5'-((S)-1-methoxymethoxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-tridecyl}-4-hydroxy-5-methyl-dihydro-furan-2-one

nonylmagnesium bromide

(-)-(2R,3R,6R,7R,10R,11S)-11,12-Dihydroxy-1,2:3,6:7,10-triepoxydodecane

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