(1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane

Base Information

• Chemical Name: (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane
• CAS No.: 371783-90-3
• Molecular Formula: C₂₉H₄₇BrO₃Si₂
• Molecular Weight: 579.765
• Mol file: 371783-90-3.mol

Synonyms:

Chemical Property of (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane

There total 8 articles about (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (1R)-1-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-bromoethan-1-ol (371783-87-8) → (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane (371783-90-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 8h;

DOI:10.1248/cpb.49.1018

Reference yield:

1-(3-chloromethyl-4-hydroxyphenyl)ethanone (24085-05-0) → (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane (371783-90-3)

Guidance literature:

Multi-step reaction with 7 steps

1: dimethylsulfoxide / 1 h / 60 °C

2: aq. NaOH / 2 h / Heating

3: 87 percent / H₂SO₄ / 1 h / Heating

4: 78 percent / KI; K₂CO₃ / dimethylformamide / 1.5 h / 50 °C

5: 72 percent / Br₂ / hexane; ethyl acetate / 0.5 h

6: 86 percent / Al(OEt)3; (R)-α,α-diphenyl-2-pyrrolidinylmethanol; BH3*Me2S / tetrahydrofuran / 2 h / 50 °C

7: imidazole / toluene; dimethylformamide / 8 h / 20 °C

With 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; sulfuric acid; bromine; aluminum ethoxide; potassium carbonate; (R)-α,α-diphenylprolinol; potassium iodide; In tetrahydrofuran; hexane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.49.1018

Reference yield:

5-acetyl-2-hydroxyphenylacetonitrile (65236-06-8) → (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane (371783-90-3)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. NaOH / 2 h / Heating

2: 87 percent / H₂SO₄ / 1 h / Heating

3: 78 percent / KI; K₂CO₃ / dimethylformamide / 1.5 h / 50 °C

4: 72 percent / Br₂ / hexane; ethyl acetate / 0.5 h

5: 86 percent / Al(OEt)3; (R)-α,α-diphenyl-2-pyrrolidinylmethanol; BH3*Me2S / tetrahydrofuran / 2 h / 50 °C

6: imidazole / toluene; dimethylformamide / 8 h / 20 °C

With 1H-imidazole; sodium hydroxide; dimethylsulfide borane complex; sulfuric acid; bromine; aluminum ethoxide; potassium carbonate; (R)-α,α-diphenylprolinol; potassium iodide; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1248/cpb.49.1018

upstream raw materials:

tert-butyldimethylsilyl chloride

(1R)-1-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-bromoethan-1-ol

1-(3-chloromethyl-4-hydroxyphenyl)ethanone

5-acetyl-2-hydroxyphenylacetonitrile

Downstream raw materials:

2-{[(2S)-2-({(2R)-2-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-tert-butyldimethylsilyloxyethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide

2-{[(2S)-2-({(2R)-2-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-hydroxyethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide