2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate

Base Information

• Chemical Name: 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate
• CAS No.: 807373-52-0
• Molecular Formula: C₂₃H₃₇BrCl₃NO₃Si
• Molecular Weight: 589.9
• Mol file: 807373-52-0.mol

Synonyms:2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate

Chemical Property of 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate

There total 4 articles about 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate 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%

2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-hydroxypentyl}(methyl)carbamate (807373-38-2) → 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate (807373-52-0)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo048848j

Reference yield:

2-{(6S)-6-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone → 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate (807373-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / K₂CO₃ / acetonitrile / 48 h / 20 °C

2: OsO₄; NaIO₄ / dioxane; H₂O / 4 h / 20 °C

3: 701 mg / NaBH₄ / ethanol / 2 h / 0 °C

4: 93 percent / PPh₃; CBr₄ / CH₂Cl₂ / 1 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; carbon tetrabromide; potassium carbonate; triphenylphosphine; In 1,4-dioxane; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo048848j

Reference yield:

{(S)-1-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-oxo-pentyl}-methyl-carbamic acid 2,2,2-trichloro-ethyl ester (1026517-23-6) → 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-bromopentyl}(methyl)carbamate (807373-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 701 mg / NaBH₄ / ethanol / 2 h / 0 °C

2: 93 percent / PPh₃; CBr₄ / CH₂Cl₂ / 1 h / 0 °C

With sodium tetrahydroborate; carbon tetrabromide; triphenylphosphine; In ethanol; dichloromethane;

DOI:10.1021/jo048848j

upstream raw materials:

2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-5-hydroxypentyl}(methyl)carbamate

{(S)-1-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-ethyl]-5-oxo-pentyl}-methyl-carbamic acid 2,2,2-trichloro-ethyl ester

2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-7-oxo-7-phenylhept-5(Z)-enyl}(methyl)carbamate

Downstream raw materials:

(-)-sedamine

(2S)-2-((2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethyl)-1-methylpiperidine