(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

Base Information

Chemical Name:(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester
CAS No.:434938-19-9
Molecular Formula:C₁₉H₂₃Cl₃O₆
Molecular Weight:453.747
Hs Code.:

Synonyms:(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

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Chemical Property of (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

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Technology Process of (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

There total 3 articles about (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl 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: 78.0%

: 434938-18-8
(E)-(4R,5S)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

: 434938-19-9
(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

Guidance literature:: With water; acetic acid; In tetrahydrofuran; at 80 ℃; for 12h;
DOI:10.3987/com-01-9391

Reference yield:

: 434938-15-5
(S)-3-Hydroxy-butyric acid 2,2,2-trichloro-ethyl ester

: 434938-19-9
(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 48 h / 20 °C

2: 78 percent / H₂O; AcOH / tetrahydrofuran / 12 h / 80 °C

With dmap; (1S)-10-camphorsulfonic acid; water; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1: Keck procedure;
DOI:10.3987/com-01-9391

Reference yield:

: 2,2,2-trichloroethyl (S)-3-tertbutyldimethylsiloxybutanoate

: 434938-19-9
(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (S)-1-methyl-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / H₂O; AcOH / tetrahydrofuran / 12 h / 80 °C

2: 87 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 48 h / 20 °C

3: 78 percent / H₂O; AcOH / tetrahydrofuran / 12 h / 80 °C

With dmap; (1S)-10-camphorsulfonic acid; water; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 2: Keck procedure;
DOI:10.3987/com-01-9391