Carbamic acid, [(1S,5Z)-1-[(2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenylethyl]-7 -oxo-7-phenyl-5-heptenyl]methyl-, 2,2,2-trichloroethyl ester

Base Information

• Chemical Name: Carbamic acid, [(1S,5Z)-1-[(2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenylethyl]-7 -oxo-7-phenyl-5-heptenyl]methyl-, 2,2,2-trichloroethyl ester
• CAS No.: 807373-27-9
• Molecular Formula: C31H42Cl3NO4Si
• Molecular Weight: 627.123
• Mol file: 807373-27-9.mol

Synonyms:

Chemical Property of Carbamic acid, [(1S,5Z)-1-[(2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenylethyl]-7 -oxo-7-phenyl-5-heptenyl]methyl-, 2,2,2-trichloroethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbamic acid, [(1S,5Z)-1-[(2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenylethyl]-7 -oxo-7-phenyl-5-heptenyl]methyl-, 2,2,2-trichloroethyl ester

There total 2 articles about Carbamic acid, [(1S,5Z)-1-[(2S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-phenylethyl]-7 -oxo-7-phenyl-5-heptenyl]methyl-, 2,2,2-trichloroethyl 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: 100.0%

2-{(6S)-6-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-7-oxo-7-phenylhept-5(Z)-enyl}(methyl)carbamate (807373-27-9)

Guidance literature:

With potassium carbonate; In acetonitrile; at 20 ℃; for 48h;

DOI:10.1021/jo048848j

Reference yield:

(cis:trans)-(-)-lobeline (1070913-26-6) + tert-butyldimethylsilyl chloride (18162-48-6) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → 2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-7-oxo-7-phenylhept-5(Z)-enyl}(methyl)carbamate (807373-27-9)

Guidance literature:

(cis:trans)-(-)-lobeline; tert-butyldimethylsilyl chloride; With dmap; triethylamine; In dichloromethane; Inert atmosphere;

2,2,2-Trichloroethyl chloroformate; With potassium carbonate; In acetonitrile; Inert atmosphere;

DOI:10.1021/ja804738b

Reference yield:

2,2,2-trichloroethyl {(1S)-1-[(2S)-2-(tert-butyldimethylsilanoxy)-2-phenylethyl]-7-oxo-7-phenylhept-5(Z)-enyl}(methyl)carbamate (807373-27-9) → (2S)-2-((2S)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-phenylethyl)-1-methylpiperidine (807373-66-6)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 93 percent / PPh₃; CBr₄ / CH₂Cl₂ / 1 h / 0 °C

4: 96 percent / Zn; acetic acid / CH₂Cl₂ / 4 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; carbon tetrabromide; acetic acid; triphenylphosphine; zinc; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1021/jo048848j

upstream raw materials:

2,2,2-Trichloroethyl chloroformate

(cis:trans)-(-)-lobeline

tert-butyldimethylsilyl chloride

Downstream raw materials:

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

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

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

(-)-sedamine