(E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

Base Information

Chemical Name:(E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester
CAS No.:185424-26-4
Molecular Formula:C₁₅H₁₇F₃O₄
Molecular Weight:318.293
Hs Code.:

Synonyms:(E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

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Chemical Property of (E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

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Technology Process of (E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

There total 3 articles about (E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl 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: 73.0%

: 185423-98-7
((Z)-(R)-1-Benzyloxymethyl-4,4,4-trifluoro-but-2-enyloxy)-acetic acid methyl ester

: 185424-26-4
(E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;
DOI:10.1021/jo961246i

Reference yield:

: (Z)-(R)-1-Benzyloxy-5,5,5-trifluoro-pent-3-en-2-ol

: 185424-26-4
(E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1.) THF, 0 deg C, 10 min, 2.) THF, room temp., overnight

2: 1.) (COCl)2, DMF, 2.) pyridine / 1.) CH₂Cl₂, overnight, room temp., 2.) CH₂Cl₂, room temp., overnight

3: 73 percent / diisopropylamine, n-BuLi, HMPA / tetrahydrofuran; hexane / 0.17 h / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; sodium hydride; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane;
DOI:10.1021/jo961246i

Reference yield:

: 1025888-21-4
((Z)-(R)-1-Benzyloxymethyl-4,4,4-trifluoro-but-2-enyloxy)-acetic acid

: 185424-26-4
(E)-(2S,3S)-6-Benzyloxy-2-hydroxy-3-trifluoromethyl-hex-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMF, 2.) pyridine / 1.) CH₂Cl₂, overnight, room temp., 2.) CH₂Cl₂, room temp., overnight

2: 73 percent / diisopropylamine, n-BuLi, HMPA / tetrahydrofuran; hexane / 0.17 h / -78 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; hexane;
DOI:10.1021/jo961246i