(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

Base Information

Chemical Name:(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester
CAS No.:92220-11-6
Molecular Formula:C₂₆H₃₆O₉SSi
Molecular Weight:552.718
Hs Code.:

(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

Synonyms:(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

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Chemical Property of (2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

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Technology Process of (2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

There total 8 articles about (2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-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: 81.0%

: C₁₆H₂₆O₅Si

: 92220-10-5
2-(p-Tolylsulfonyl)ethyl 5-Hydroxy-3-methyl-2(S),3(R)-epoxypentanoate

: 92220-11-6
(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

Guidance literature:: With dmap; In dichloromethane; at 25 ℃; for 13h;
DOI:10.1021/jo00197a002

Reference yield:

: 35066-36-5
5-hydroxy-3-methyl-2-(E)-pentenoic acid methyl ester

: 92220-11-6
(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / dimethylformamide / 13 h / 25 °C

2: Dibal-H (1 M hexane solution) / diethyl ether / 1) -78 deg C, 10 min, 2) 25 deg C, 1.5 h

3: 81 percent / (-)-diethyl tartrate, titanium(IV)isopropoxide, tert-butyl hydroperoxide (3.98 M toluene solution) / CH₂Cl₂ / 17 h / -20 °C

4: KMnO₄, Bu₄NBr / H₂O; benzene / 28 h / 25 °C

5: 56 percent / triethylamine, N,N-bis<2-oxo-3-oxazolidinyl>phosphorodiamidic chloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

6: 95 percent / acetic acid; H₂O; tetrahydrofuran / 5 h / 25 °C

7: 81 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 25 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; potassium permanganate; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; tetrabutylammomium bromide; diisobutylaluminium hydride; (-)-diethyl tartrate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00197a002

Reference yield:

: 92220-19-4
(2S,3R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-methyl-oxirane-2-carboxylic acid

: 92220-11-6
(2E,4Z)-Hexa-2,4-dienedioic acid 2-{(2R,3S)-2-methyl-3-[2-(toluene-4-sulfonyl)-ethoxycarbonyl]-oxiranyl}-ethyl ester 2-trimethylsilanyl-ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 56 percent / triethylamine, N,N-bis<2-oxo-3-oxazolidinyl>phosphorodiamidic chloride, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 25 °C

2: 95 percent / acetic acid; H₂O; tetrahydrofuran / 5 h / 25 °C

3: 81 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 13 h / 25 °C

With dmap; N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid;
DOI:10.1021/jo00197a002