(E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

Base Information

Chemical Name:(E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester
CAS No.:301686-13-5
Molecular Formula:C₂₀H₂₀O₆S
Molecular Weight:388.441
Hs Code.:

Synonyms:(E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

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Chemical Property of (E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

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Technology Process of (E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

There total 4 articles about (E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic 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: 96.0%

: 98-59-9
p-toluenesulfonyl chloride

: 301686-12-4
(E)-3-[2-((2S,3S)-3-Hydroxymethyl-oxiranyl)-phenyl]-acrylic acid methyl ester

: 301686-13-5
(E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1016/S0040-4039(00)01047-9

Reference yield:

: 115984-41-3,61198-30-9,115984-39-9
(E)-3-[2-{(E)-2-methoxycarbonylvinyl}phenyl]acrylic acid methyl ester

: 301686-13-5
(E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / diisobutylaluminum hydride (DIBALH) / toluene; CH₂Cl₂ / -78 °C

2: L-(+)-DIPT; t-BuO₂H; 4 Angstroem MS / Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane

3: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

With tert.-butylhydroperoxide; dmap; L-(+)-diisopropyl tartrate; 4 Angstroem MS; diisobutylaluminium hydride; triethylamine; titanium(IV) isopropylate; In 2,2,4-trimethylpentane; dichloromethane; toluene; 1: Reduction / 2: Sharpless-Katsuki asymmetric epoxidation / 3: Tosylation;
DOI:10.1016/S0040-4039(00)01047-9

Reference yield:

: 301686-08-8
(E)-3-[2-((E)-3-Hydroxy-propenyl)-phenyl]-acrylic acid methyl ester

: 301686-13-5
(E)-3-{2-[(2S,3S)-3-(Toluene-4-sulfonyloxymethyl)-oxiranyl]-phenyl}-acrylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: L-(+)-DIPT; t-BuO₂H; 4 Angstroem MS / Ti(OiPr)4 / CH₂Cl₂; 2,2,4-trimethyl-pentane

2: 96 percent / Et₃N; DMAP / CH₂Cl₂ / 0 °C

With tert.-butylhydroperoxide; dmap; L-(+)-diisopropyl tartrate; 4 Angstroem MS; triethylamine; titanium(IV) isopropylate; In 2,2,4-trimethylpentane; dichloromethane; 1: Sharpless-Katsuki asymmetric epoxidation / 2: Tosylation;
DOI:10.1016/S0040-4039(00)01047-9