3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

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Chemical Name:3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide
CAS No.:374570-48-6
Molecular Formula:C₂₂H₃₆O₃S₂Si
Molecular Weight:440.744
Hs Code.:

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Chemical Property of 3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

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Technology Process of 3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

There total 18 articles about 3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide 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: 87.0%

: 3634-56-8
isopropyldimethylsilyl chloride

: 374570-46-4
3-[(1S,5E,7E)-8-(1,3-dithiolan-2-yl)-1-hydroxy-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

: 374570-48-6
3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 0.833333h;
DOI:10.1016/S0040-4020(01)00686-X

Reference yield:

: 81132-09-4
(2R,3S)-1,2-O-Isopropylidenepentane-1,2,3,5-tetraol

: 374570-48-6
3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

Guidance literature:: Multi-step reaction with 17 steps

1.1: Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / 0 °C

2.1: diisopropylethylamine / CHCl₃ / 19 h / 40 °C

3.1: 4.51 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

4.1: 93 percent / PPh₃; imidazole; I₂ / tetrahydrofuran / 1 h / -18 °C

5.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

5.2: 99 percent / tetrahydrofuran; hexane / 0.5 h / -18 °C

6.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C

7.1: 1.72 g / molecular sieves 4 Angstroem; LiOH*H₂O / tetrahydrofuran / 19 h / Heating

8.1: DIBALH / CH₂Cl₂; toluene / 0.25 h / -78 °C

9.1: 9.66 g / MnO₂ / CH₂Cl₂ / 0.42 h / 0 °C

10.1: 5.11 g / BF₃*OEt₂ / CH₂Cl₂ / 1.67 h / -18 °C

11.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 0 °C

12.1: 70 percent / DMSO; SO₃*pyridine; Et₃N / CH₂Cl₂ / 6 h

13.1: 87 percent / CSA / methanol; H₂O; CH₂Cl₂ / 19 h / 0 °C

14.1: Et₃N; DMAP; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂ / 2.5 h / 0 °C

15.1: 2.27 percent / 18-crown-6; K₂CO₃ / toluene / 19 h / 0 °C

16.1: 92 percent / aq. HCl / tetrahydrofuran / 97 h / 0 °C

17.1: 87 percent / imidazole / dimethylformamide / 0.83 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; manganese(IV) oxide; lithium hydroxide; 18-crown-6 ether; pyridine-SO₃ complex; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; 7.1: Horner-Emmons reaction / 15.1: intramolecular Horner-Emmons reaction;
DOI:10.1016/S0040-4020(01)00686-X

Reference yield:

: 374570-32-8
(2R,3S)-1,2-(isopropylidenedioxy)-3-(methoxymethoxy)-5-pentanol

: 374570-48-6
3-[(1S,5E,7E)-1-(dimethylisopropyl)silyloxy-8-(1,3-dithiolan-2-yl)-4,4-dimethyl-5,7-octadienyl]-2-buten-4-olide

Guidance literature:: Multi-step reaction with 14 steps

1.1: 93 percent / PPh₃; imidazole; I₂ / tetrahydrofuran / 1 h / -18 °C

2.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 99 percent / tetrahydrofuran; hexane / 0.5 h / -18 °C

3.1: diisobutylaluminium hydride / toluene / 0.5 h / -78 °C

4.1: 1.72 g / molecular sieves 4 Angstroem; LiOH*H₂O / tetrahydrofuran / 19 h / Heating

5.1: DIBALH / CH₂Cl₂; toluene / 0.25 h / -78 °C

6.1: 9.66 g / MnO₂ / CH₂Cl₂ / 0.42 h / 0 °C

7.1: 5.11 g / BF₃*OEt₂ / CH₂Cl₂ / 1.67 h / -18 °C

8.1: 89 percent / Et₃N; DMAP / CH₂Cl₂ / 19 h / 0 °C

9.1: 70 percent / DMSO; SO₃*pyridine; Et₃N / CH₂Cl₂ / 6 h

10.1: 87 percent / CSA / methanol; H₂O; CH₂Cl₂ / 19 h / 0 °C

11.1: Et₃N; DMAP; 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride / CH₂Cl₂ / 2.5 h / 0 °C

12.1: 2.27 percent / 18-crown-6; K₂CO₃ / toluene / 19 h / 0 °C

13.1: 92 percent / aq. HCl / tetrahydrofuran / 97 h / 0 °C

14.1: 87 percent / imidazole / dimethylformamide / 0.83 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; manganese(IV) oxide; lithium hydroxide; 18-crown-6 ether; pyridine-SO₃ complex; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: Horner-Emmons reaction / 12.1: intramolecular Horner-Emmons reaction;
DOI:10.1016/S0040-4020(01)00686-X