2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester

Base Information

• Chemical Name: 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester
• CAS No.: 312962-25-7
• Molecular Formula: C₃₈H₅₈O₇Si
• Molecular Weight: 654.96
• Mol file: 312962-25-7.mol

Synonyms:2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester

Chemical Property of 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester

There total 17 articles about 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl 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: 89.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2-allyl-6-hydroxy-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester (312962-21-3) → 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester (312962-25-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/ol006646d

Reference yield:

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester (312962-25-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / pyridine

2: 83 percent / KOMe / PdCl₂(dppf) / tetrahydrofuran

3: 96 percent / BCl₃ / CH₂Cl₂ / 5 h / 20 °C

4: 88 percent / DEAD; PPh₃ / diethyl ether / 20 h / 20 °C

5: 89 percent / imidazole / dimethylformamide / 24 h / 20 °C

With pyridine; 1H-imidazole; potassium methanolate; boron trichloride; triphenylphosphine; diethylazodicarboxylate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Substitution / 3: Ring cleavage / 4: Esterification / 5: Substitution;

DOI:10.1021/ol006646d

Reference yield:

2,6-Dihydroxybenzoic acid (303-07-1) → 2-allyl-6-(tert-butyl-dimethyl-silanyloxy)-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester (312962-25-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / SOCl₂; DMAP / 1,2-dimethoxy-ethane

2: 85 percent / pyridine

3: 83 percent / KOMe / PdCl₂(dppf) / tetrahydrofuran

4: 96 percent / BCl₃ / CH₂Cl₂ / 5 h / 20 °C

5: 88 percent / DEAD; PPh₃ / diethyl ether / 20 h / 20 °C

6: 89 percent / imidazole / dimethylformamide / 24 h / 20 °C

With pyridine; 1H-imidazole; dmap; thionyl chloride; potassium methanolate; boron trichloride; triphenylphosphine; diethylazodicarboxylate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Cyclization / 2: Substitution / 3: Substitution / 4: Ring cleavage / 5: Esterification / 6: Substitution;

DOI:10.1021/ol006646d

upstream raw materials:

tert-butyldimethylsilyl chloride

2-allyl-6-hydroxy-benzoic acid (1R,3S,4R)-1-[2-(4-methoxy-benzyloxy)-ethyl]-3-methoxymethoxy-4,7-dimethyl-oct-6-enyl ester

2,6-Dihydroxybenzoic acid

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one