(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

Base Information

Chemical Name:(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester
CAS No.:701262-90-0
Molecular Formula:C₂₉H₄₂O₉SSi
Molecular Weight:594.799
Hs Code.:

Synonyms:(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

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Chemical Property of (E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

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Technology Process of (E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

There total 17 articles about (E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-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: 92.0%

: 701262-89-7
(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-4-trimethylsilanyl-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

: 701262-90-0
(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

Guidance literature:: With potassium carbonate; In tetrahydrofuran; methanol; at 0 ℃;
DOI:10.1002/hlca.200490062

Reference yield:

: 84028-77-3
(3-methoxycarbonylpropionyl)methylenetriphenylphosphorane

: 701262-90-0
(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: toluene / 70 - 80 °C

2: 74 percent / DMAP / CH₂Cl₂; triethylamine / 0 - 20 °C

3: 92 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.42 h / 0 °C

With dmap; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; triethylamine; toluene; 1: Wittig reaction;
DOI:10.1016/j.tet.2007.03.144

Reference yield:

: 78010-00-1
2,3-O-isopropylidene-D-arabinose diethyl dithio acetal

: 701262-90-0
(E)-6-{(4R,5S)-2,2-Dimethyl-5-[(1S,2S)-2-(toluene-4-sulfonyloxy)-1-triethylsilanyloxy-but-3-ynyl]-[1,3]dioxolan-4-yl}-4-oxo-hex-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 77 percent / Et₃N / CH₂Cl₂ / 20 °C

2.1: 95 percent / imidazole / dimethylformamide / 20 °C

3.1: 91 percent / DIBAL-H / cyclohexane; CH₂Cl₂ / 0.5 h / -78 °C

4.1: 82 percent / SO₃*Py; i-Pr₂NEt / dimethylsulfoxide; CH₂Cl₂ / 0 - 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

5.2: 791 mg / hexane; tetrahydrofuran / 3 h / -78 °C

6.1: 558 mg / I₂; NaHCO₃ / acetone; H₂O / 0.33 h / 0 °C

7.1: toluene / 70 - 80 °C

8.1: 74 percent / DMAP / CH₂Cl₂; triethylamine / 0 - 20 °C

9.1: 92 percent / K₂CO₃ / methanol; tetrahydrofuran / 0.42 h / 0 °C

With 1H-imidazole; dmap; n-butyllithium; pyridine-SO₃ complex; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; acetone; toluene; 7.1: Wittig reaction;
DOI:10.1016/j.tet.2007.03.144