(3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Base Information

• Chemical Name: (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane
• CAS No.: 159848-85-8
• Molecular Formula: C₃₄H₅₀Cl₃NO₈Si
• Molecular Weight: 735.217
• Mol file: 159848-85-8.mol

Synonyms:

Chemical Property of (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

There total 18 articles about (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane 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: 99.0%

[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-phenyl)-propyl]-[(S)-3-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester (159848-84-7) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane (159848-85-8)

Guidance literature:

With pyridine; dmap; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85520-4

Reference yield:

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane (159848-85-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / AD-mix-β, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 4 deg C, 11 h then rt., 4 h

2: 73 percent / pyridine / 18 h / 4 °C

3: 87 percent / LiCl / dimethylformamide / 14 h / 85 °C

4: 91 percent / HCO₂NH₄ / 5percent Pd-C / methanol / 2 h / 0 °C

5: 99.6 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

6: 95 percent / 1.5M DIBAL / CH₂Cl₂; toluene / 0.25 h / -78 °C

7: 74 percent / 1M NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 10 h / 0 - 10 °C

8: 99.6 percent / Et₃N / dioxane / 14 h / 50 °C

9: 245 mg / 2M LiBH₄ / tetrahydrofuran; diethyl ether / 15 h / Ambient temperature

10: 99 percent / DMAP, pyridine / 20 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium borohydride; methanesulfonamide; AD-mix-β; ammonium formate; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)85520-4

Reference yield:

ethyl (2RS,3R)-2-chloro-3-hydroxy-3-(4-methoxyphenyl)propionate → (3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane (159848-85-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / HCO₂NH₄ / 5percent Pd-C / methanol / 2 h / 0 °C

2: 99.6 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

3: 95 percent / 1.5M DIBAL / CH₂Cl₂; toluene / 0.25 h / -78 °C

4: 74 percent / 1M NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 10 h / 0 - 10 °C

5: 99.6 percent / Et₃N / dioxane / 14 h / 50 °C

6: 245 mg / 2M LiBH₄ / tetrahydrofuran; diethyl ether / 15 h / Ambient temperature

7: 99 percent / DMAP, pyridine / 20 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; lithium borohydride; ammonium formate; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)85520-4

upstream raw materials:

[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-phenyl)-propyl]-[(S)-3-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester

2,2,2-Trichloroethyl chloroformate

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

(S)-β-amino-β-(4-methoxyphenyl)propionic acid

Downstream raw materials:

(3S,3'S)-3-<3'-acetoxy-N-tert-butoxycarbonyl-3'-(4-methoxyphenyl)propylamino>-3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

2'-deoxymugineic acid