(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Base Information

Chemical Name:(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide
CAS No.:691012-78-9
Molecular Formula:C₂₂H₂₅ClINO₆
Molecular Weight:561.801
Hs Code.:

Synonyms:(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

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Chemical Property of (R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

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Technology Process of (R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

There total 5 articles about (R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide 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: 85.0%

: 691012-77-8
3-[3-(tert-butyl-dimethyl-silanyloxy)-2-chloro-4-methoxy-phenyl]-3-hydroxy-N-[3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

: 691012-78-9
(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1016/j.tet.2004.02.020

Reference yield:

: 37687-57-3
2-chloro-3-hydroxy-4-methoxybenzaldehyde

: 691012-78-9
(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / imidazole / dimethylformamide / 0.75 h / 20 °C

2: 64 percent / stannous triflate; N-ethyl piperidine; chiral diamine / CH₂Cl₂ / 10 h / -95 °C

3: 88 percent / CH₂Cl₂ / 2 h / 20 °C

4: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With 1-ethyl-piperidine; 1H-imidazole; tin(II) trifluoromethanesulfonate; chiral diamine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: asymmetric Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2004.02.020

Reference yield:

: 691012-74-5
3-(tert-butyl-dimethyl-silanyloxy)-2-chloro-4-methoxy-benzaldehyde

: 691012-78-9
(R)-3-(2-Chloro-3-hydroxy-4-methoxy-phenyl)-3-hydroxy-N-[(E)-3-iodo-4-(4-methoxy-benzyloxy)-but-2-enyl]-propionamide

Guidance literature:: Multi-step reaction with 3 steps

1: 64 percent / stannous triflate; N-ethyl piperidine; chiral diamine / CH₂Cl₂ / 10 h / -95 °C

2: 88 percent / CH₂Cl₂ / 2 h / 20 °C

3: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; chiral diamine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; 1: asymmetric Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2004.02.020