(3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate

Base Information

• Chemical Name: (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate
• CAS No.: 133619-15-5
• Molecular Formula: C₂₀H₂₄O₃Si
• Molecular Weight: 340.494
• Mol file: 133619-15-5.mol

Synonyms:(3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate

Chemical Property of (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate

There total 4 articles about (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate 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: 45.0%

3-(1-dimethylphenylsilyl-1-butene) (2R)-2-O-acetyl-2-phenylacetate (133619-14-4,133633-87-1) → (3R)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate (133619-16-6) + (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate (133619-15-5)

Guidance literature:

With sodium hydrogensulfide; In methanol; water; at 60 ℃; for 48h;

DOI:10.1016/S0957-4166(00)80446-2

Reference yield:

dimethyl(phenyl)silyllithium (3839-31-4) → (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate (133619-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / tetrahydrofuran / -100 °C

2: 95 percent / dicyclohexylcarbodiimide (DCC), dimethylaminopropylamine (DMAP) / CH₂Cl₂ / 6 h / 0 - 25 °C

3: 90 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / Ambient temperature

4: 45 percent / NaHS / methanol; H₂O / 48 h / 60 °C

With sodium hydrogensulfide; boron trifluoride diethyl etherate; 1-amino-3-(dimethylamino)propane; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/S0957-4166(00)80446-2

Reference yield:

(E)-1-(phenyldimethylsilyl)-2-buten-1-ol (96720-38-6) → (3S)-3-(1-dimethylphenylsilyl-1-butene) (2R)-2-hydroxy-2-phenylacetate (133619-15-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / dicyclohexylcarbodiimide (DCC), dimethylaminopropylamine (DMAP) / CH₂Cl₂ / 6 h / 0 - 25 °C

2: 90 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / Ambient temperature

3: 45 percent / NaHS / methanol; H₂O / 48 h / 60 °C

With sodium hydrogensulfide; boron trifluoride diethyl etherate; 1-amino-3-(dimethylamino)propane; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water;

DOI:10.1016/S0957-4166(00)80446-2

upstream raw materials:

3-(1-dimethylphenylsilyl-1-butene) (2R)-2-O-acetyl-2-phenylacetate

dimethyl(phenyl)silyllithium

(E)-1-(phenyldimethylsilyl)-2-buten-1-ol

1-(1-dimethylphenylsilyl-2-butene) (2R)-2-O-acetyl-2-phenylacetate

Downstream raw materials:

(R)-(E)-1-(dimethylphenylsilyl)-1-buten-3-ol