(4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

Base Information

Chemical Name:(4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one
CAS No.:137266-22-9
Molecular Formula:C₂₃H₃₂Cl₂O₂SSi
Molecular Weight:471.563
Hs Code.:

Synonyms:(4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

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Chemical Property of (4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

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Technology Process of (4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

There total 1 articles about (4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one 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: 89.0%

: 137266-21-8
Trimethyl-[(1E,5E,7E)-4,4,6-trimethyl-8-((S)-toluene-4-sulfinyl)-octa-1,5,7-trienyl]-silane

: 76-02-8
trifluoroacetyl chloride

: 137266-22-9
(4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

Guidance literature:: With copper; zinc; In tetrahydrofuran; at -40 ℃;
DOI:10.1016/S0040-4039(00)92273-1

Reference yield:

: 137266-22-9
(4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

: 16772-63-7
(-)-pereniporin B

Guidance literature:: Multi-step reaction with 15 steps

1: 89 percent / Bu₃SnH, AIBN / benzene / Heating

2: 82 percent / 1) LDA / tetrahydrofuran / -78 °C

3: 92 percent / LiOH / methanol; H₂O / 25 °C

4: 1) i-BuOCOCl, Et₃N 2) NaBH₄ / 1) THF, -25 deg C 2) DMF, -30 deg C

5: 1) (COCl)2, DMSO 2) Et₃N / 1) CH₂Cl₂, -78 deg C 2) -78 to 25 deg C

6: 1) Me₂SO₄ 2) 4 Angstroem zeolites / 1) DMF, 70 deg C 2) 25 deg C

7: 1) LiAlH₄ 2) p-TsCl, pyridine / 1) Et₂O, 0 deg C 2) 25 deg C

8: 85 percent / TiCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

10: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C 2) -78 to 25 deg C

11: 100 percent / H₂ / 10percent Pd-C / ethyl acetate

12: 1) 3N>Br₃ 2) DBU / 1) THF, 25 deg C 2) PhH, reflux

13: 66 percent / (PhSeO)2O / chlorobenzene / 0.08 h / 125 - 130 °C

14: Dibal-H / toluene / -78 °C

15: Ag₂CO₃, Celite / benzene / Heating

With pyridine; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); (PhSeO)2O; 4 Angstroem zeolites; Celite; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; phenyltrimethylammonium tribromide; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; dimethyl sulfate; silver carbonate; lithium diisopropyl amide; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; chlorobenzene; toluene; benzene;
DOI:10.1016/S0040-4039(00)92273-1

Reference yield:

: 137266-22-9
(4S,5S)-3,3-Dichloro-5-p-tolylsulfanyl-4-((1E,5E)-1,3,3-trimethyl-6-trimethylsilanyl-hexa-1,5-dienyl)-dihydro-furan-2-one

: 24179-85-9
(+)-fragrolide

Guidance literature:: Multi-step reaction with 12 steps

1: 89 percent / Bu₃SnH, AIBN / benzene / Heating

2: 82 percent / 1) LDA / tetrahydrofuran / -78 °C

3: 92 percent / LiOH / methanol; H₂O / 25 °C

4: 1) i-BuOCOCl, Et₃N 2) NaBH₄ / 1) THF, -25 deg C 2) DMF, -30 deg C

5: 1) (COCl)2, DMSO 2) Et₃N / 1) CH₂Cl₂, -78 deg C 2) -78 to 25 deg C

6: 1) Me₂SO₄ 2) 4 Angstroem zeolites / 1) DMF, 70 deg C 2) 25 deg C

7: 1) LiAlH₄ 2) p-TsCl, pyridine / 1) Et₂O, 0 deg C 2) 25 deg C

8: 85 percent / TiCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

10: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C 2) -78 to 25 deg C

11: 100 percent / H₂ / 10percent Pd-C / ethyl acetate

12: 1) 3N>Br₃ 2) DBU / 1) THF, 25 deg C 2) PhH, reflux

With pyridine; lithium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); 4 Angstroem zeolites; hydrogen; tri-n-butyl-tin hydride; titanium tetrachloride; phenyltrimethylammonium tribromide; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; dimethyl sulfate; lithium diisopropyl amide; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1016/S0040-4039(00)92273-1