(E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester
• CAS No.: 204575-82-6
• Molecular Formula: C₁₄H₁₈O₆S
• Molecular Weight: 314.359

Synonyms:(E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester

Chemical Property of (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester

Chemical Property:

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Technology Process of (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester

There total 2 articles about (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid 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: 72.0%

(S)-ethyl trans-4,5-dihydroxylpent-2-enoate (10446-09-0,69010-16-8,89941-81-1,124819-67-6,150739-00-7,64520-62-3) + p-toluenesulfonyl chloride (98-59-9) → (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester (204575-82-6)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00008-8

Reference yield:

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (64520-58-7,917877-01-1) → (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester (204575-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / aq. HCl / ethanol / 2 h / Ambient temperature

2: 72 percent / 2,4,6-collidine / CH₂Cl₂ / 20 h / Ambient temperature

With 2,4,6-trimethyl-pyridine; hydrogenchloride; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)00008-8

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + (E)-(S)-4-Hydroxy-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester (204575-82-6) → (E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester (204575-69-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(98)00008-8

upstream raw materials:

(S)-ethyl trans-4,5-dihydroxylpent-2-enoate

p-toluenesulfonyl chloride

ethyl (E)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

Downstream raw materials:

(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(toluene-4-sulfonyloxy)-pent-2-enoic acid ethyl ester

[(3S,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-isoxazolidin-3-yl]-acetic acid ethyl ester

[(3R,4S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-isoxazolidin-3-yl]-acetic acid ethyl ester

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