(4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester

Base Information

• Chemical Name: (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester
• CAS No.: 241155-48-6
• Molecular Formula: C₄₇H₇₆O₇Si₂
• Molecular Weight: 809.287
• Mol file: 241155-48-6.mol

Synonyms:(4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester

Chemical Property of (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester

There total 25 articles about (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl 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: 85.0%

(4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (241155-40-8) + (E)-(2S,3R)-6-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dien-1-ol (241155-47-5) → (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester (241155-48-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 ℃; for 24h;

DOI:10.1055/s-1999-2743

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester (241155-48-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 83 percent / imidazole / dimethylformamide

2: 92 percent / DIBAL-H / CH₂Cl₂

3: 95 percent / toluene

4: 83 percent / DIBAL-H / CH₂Cl₂

5: 95 percent / Ti(O-i-Pr)4, (-)-diethyl tartrate, t-BuOOH, molecular sieves 4 Angstroem / CH₂Cl₂

6: 94 percent / NaH, Bu₄NI / 2.5 h / 0 - 20 °C

7: 85 percent / n-BuLi / toluene / 48 h / -78 - 20 °C

8: H₂ / 10 percent Pd/C / ethyl acetate / 2.5 h / Ambient temperature

9: NaIO₄, H₂O / tetrahydrofuran / 0.04 h / Ambient temperature

10: toluene / 16 h / Ambient temperature

11: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h

12: 90 percent / DIBAL-H / toluene / 2 h / -78 °C

13: 91 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

14: 98 percent / NaClO₂, Na₂HPO₄, 2-methyl-2-butene, H₂O / 2-methyl-propan-2-ol / 1 h

15: 85 percent / diethyl azodicarboxylate, Ph₃P / toluene / 24 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium periodate; disodium hydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 4 A molecular sieve; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1055/s-1999-2743

Reference yield:

(2R)-2-methyl-3-(triisopropylsilyloxy)propanal (241155-54-4) → (4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid (E)-(2S,3R)-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dienyl ester (241155-48-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / toluene

2: 83 percent / DIBAL-H / CH₂Cl₂

3: 95 percent / Ti(O-i-Pr)4, (-)-diethyl tartrate, t-BuOOH, molecular sieves 4 Angstroem / CH₂Cl₂

4: 94 percent / NaH, Bu₄NI / 2.5 h / 0 - 20 °C

5: 85 percent / n-BuLi / toluene / 48 h / -78 - 20 °C

6: H₂ / 10 percent Pd/C / ethyl acetate / 2.5 h / Ambient temperature

7: NaIO₄, H₂O / tetrahydrofuran / 0.04 h / Ambient temperature

8: toluene / 16 h / Ambient temperature

9: 99 percent / H₂ / 10 percent Pd/C / ethyl acetate / 2 h

10: 90 percent / DIBAL-H / toluene / 2 h / -78 °C

11: 91 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

12: 98 percent / NaClO₂, Na₂HPO₄, 2-methyl-2-butene, H₂O / 2-methyl-propan-2-ol / 1 h

13: 85 percent / diethyl azodicarboxylate, Ph₃P / toluene / 24 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium chlorite; sodium periodate; disodium hydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; 4 A molecular sieve; water; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol;

DOI:10.1055/s-1999-2743

upstream raw materials:

(4R,5S)-4,5-Dimethyl-2-methylene-6-triisopropylsilanyloxy-hexanoic acid

(E)-(2S,3R)-6-Benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-hepta-4,6-dien-1-ol

triisopropylsilyl chloride

benzyloxyacetic acid