Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester

Base Information

• Chemical Name: Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester
• CAS No.: 233609-15-9
• Molecular Formula: C₂₂H₃₆O₅Si
• Molecular Weight: 408.61
• Mol file: 233609-15-9.mol

Synonyms:Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester

Chemical Property of Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester

There total 9 articles about Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-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: 93.0%

benzaldehyde (100-52-7) + (4S,5S)-5-Hydroxy-2,4-dimethyl-7-(2-trimethylsilanyl-ethoxymethoxy)-hept-1-en-3-one (233609-14-8) → Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester (233609-15-9)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -10 ℃;

DOI:10.1016/S0957-4166(99)00069-5

Reference yield:

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene (89046-67-3,91796-47-3,91796-48-4,91798-02-6,91798-03-7,94233-73-5,94233-74-6,106357-32-8) → Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester (233609-15-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 88 percent / imidazole / dimethylformamide / 35 °C

2: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 2.) MeOH, 0 deg C

3: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 40 °C

4: 98 percent / H₂ / Pd/C / ethyl acetate

5: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

6: tetrahydrofuran / 0 - 20 °C

7: 83 percent / TBAF, 4A ms / tetrahydrofuran

8: 82 percent / DDQ / benzene / 48 h / 60 °C

9: 93 percent / SmI₂ / tetrahydrofuran / -10 °C

With 1H-imidazole; sodium tetrahydroborate; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0957-4166(99)00069-5

Reference yield:

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane (135708-75-7,135708-76-8) → Benzoic acid (1S,2R,3R)-3-hydroxy-2,4-dimethyl-1-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-pent-4-enyl ester (233609-15-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 2.) MeOH, 0 deg C

2: 95 percent / i-Pr₂NEt / CH₂Cl₂ / 40 °C

3: 98 percent / H₂ / Pd/C / ethyl acetate

4: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

5: tetrahydrofuran / 0 - 20 °C

6: 83 percent / TBAF, 4A ms / tetrahydrofuran

7: 82 percent / DDQ / benzene / 48 h / 60 °C

8: 93 percent / SmI₂ / tetrahydrofuran / -10 °C

With sodium tetrahydroborate; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; ozone; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; benzene;

DOI:10.1016/S0957-4166(99)00069-5

upstream raw materials:

benzaldehyde

(4S,5S)-5-Hydroxy-2,4-dimethyl-7-(2-trimethylsilanyl-ethoxymethoxy)-hept-1-en-3-one

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane

Downstream raw materials:

C₂₉H₄₀O₆Si

C₂₃H₂₆O₅