(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Base Information

Chemical Name:(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester
CAS No.:908866-41-1
Molecular Formula:C₄₃H₆₂O₅Si₂
Molecular Weight:715.133
Hs Code.:

(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Synonyms:(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

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Chemical Property of (E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

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Technology Process of (E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

There total 18 articles about (E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl 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:

: 908865-90-7
(2S,3S)-6-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-hexane-1,3-diol

: 908866-41-1
(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: CSA / CH₂Cl₂ / 1 h / 20 °C

2.1: 5.99 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - -40 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

4.1: 675.3 mg / dimethylsulfoxide / 2.5 h / 60 °C

5.1: 90 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

6.1: 97 percent / toluene / 0.5 h / 100 °C

7.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: 88 percent / (+)-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 1.17 h / -40 °C

9.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

10.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

10.2: 7.71 g / tetrahydrofuran / 0.5 h / 0 °C

11.1: DDQ; water / CH₂Cl₂ / 7 h / 0 - 20 °C

12.1: 10.37 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

13.1: (Sia)2BH / tetrahydrofuran / 1.5 h / 0 °C

13.2: 92 percent / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 0 - 20 °C

14.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.83 h / 0 °C

15.1: 3.87 g / toluene / 19 h / 45 - 60 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; (Sia)2BH; camphor-10-sulfonic acid; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; decane; hexane; dichloromethane; dimethyl sulfoxide; toluene; 6.1: Wittig reaction / 8.1: Sharpless epoxidation / 10.2: Wittig olefination / 15.1: Wittig reaction;
DOI:10.1021/ja066772y

Reference yield:

: tert-Butyl-{3-[(4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane

: 908866-41-1
(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 5.99 g / DIBALH / CH₂Cl₂; hexane / 1 h / -78 - -40 °C

2.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

3.1: 675.3 mg / dimethylsulfoxide / 2.5 h / 60 °C

4.1: 90 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

5.1: 97 percent / toluene / 0.5 h / 100 °C

6.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

7.1: 88 percent / (+)-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 1.17 h / -40 °C

8.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

9.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

9.2: 7.71 g / tetrahydrofuran / 0.5 h / 0 °C

10.1: DDQ; water / CH₂Cl₂ / 7 h / 0 - 20 °C

11.1: 10.37 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

12.1: (Sia)2BH / tetrahydrofuran / 1.5 h / 0 °C

12.2: 92 percent / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 0 - 20 °C

13.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.83 h / 0 °C

14.1: 3.87 g / toluene / 19 h / 45 - 60 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; (Sia)2BH; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; decane; hexane; dichloromethane; dimethyl sulfoxide; toluene; 5.1: Wittig reaction / 7.1: Sharpless epoxidation / 9.2: Wittig olefination / 14.1: Wittig reaction;
DOI:10.1021/ja066772y

Reference yield:

: 908865-92-9
(2S,3S)-6-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-methyl-hexan-1-ol

: 908866-41-1
(E)-4-{(2R,3S,5S,6S)-6-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-2,5-dimethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: Et₃N / CH₂Cl₂ / 1 h / 20 °C

2.1: 675.3 mg / dimethylsulfoxide / 2.5 h / 60 °C

3.1: 90 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

4.1: 97 percent / toluene / 0.5 h / 100 °C

5.1: 100 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

6.1: 88 percent / (+)-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves 4 Angstroem / CH₂Cl₂; decane / 1.17 h / -40 °C

7.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.75 h / 0 °C

8.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

8.2: 7.71 g / tetrahydrofuran / 0.5 h / 0 °C

9.1: DDQ; water / CH₂Cl₂ / 7 h / 0 - 20 °C

10.1: 10.37 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

11.1: (Sia)2BH / tetrahydrofuran / 1.5 h / 0 °C

11.2: 92 percent / aq. H₂O₂; NaHCO₃ / tetrahydrofuran / 0 - 20 °C

12.1: SO₃*pyridine; Et₃N / CH₂Cl₂; dimethylsulfoxide / 0.83 h / 0 °C

13.1: 3.87 g / toluene / 19 h / 45 - 60 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; (Sia)2BH; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 4 A molecular sieve; In tetrahydrofuran; decane; hexane; dichloromethane; dimethyl sulfoxide; toluene; 4.1: Wittig reaction / 6.1: Sharpless epoxidation / 8.2: Wittig olefination / 13.1: Wittig reaction;
DOI:10.1021/ja066772y