(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.:159848-86-9
Molecular Formula:C₂₈H₃₆Cl₃NO₈
Molecular Weight:620.955
Hs Code.:

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

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

Chemical Property:

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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:

: 24393-56-4
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

: 159848-86-9
(3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Guidance literature:: Multi-step reaction with 11 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

11: 134 mg / Ac₂O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h

With pyridine; 1H-imidazole; dmap; lithium borohydride; methanesulfonamide; AD-mix-β; tetrabutyl ammonium fluoride; ammonium formate; acetic anhydride; 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

: 159848-86-9
(3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Guidance literature:: Multi-step reaction with 8 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

8: 134 mg / Ac₂O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h

With pyridine; 1H-imidazole; dmap; lithium borohydride; tetrabutyl ammonium fluoride; ammonium formate; acetic anhydride; 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

Reference yield:

: 159848-77-8
ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate

: 159848-86-9
(3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane

Guidance literature:: Multi-step reaction with 10 steps

1: 73 percent / pyridine / 18 h / 4 °C

2: 87 percent / LiCl / dimethylformamide / 14 h / 85 °C

3: 91 percent / HCO₂NH₄ / 5percent Pd-C / methanol / 2 h / 0 °C

4: 99.6 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

5: 95 percent / 1.5M DIBAL / CH₂Cl₂; toluene / 0.25 h / -78 °C

6: 74 percent / 1M NaBH₃CN / methanol; acetic acid; tetrahydrofuran / 10 h / 0 - 10 °C

7: 99.6 percent / Et₃N / dioxane / 14 h / 50 °C

8: 245 mg / 2M LiBH₄ / tetrahydrofuran; diethyl ether / 15 h / Ambient temperature

9: 99 percent / DMAP, pyridine / 20 h / Ambient temperature

10: 134 mg / Ac₂O, TBAF / tetrahydrofuran / rt., 3 h then 50 deg C, 4 h then 75 deg C, 11 h

With pyridine; 1H-imidazole; dmap; lithium borohydride; tetrabutyl ammonium fluoride; ammonium formate; acetic anhydride; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; lithium chloride; 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