(5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

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Chemical Name:(5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene
CAS No.:123402-03-9
Molecular Formula:C₁₇H₁₉ClO₂SSe
Molecular Weight:401.816
Hs Code.:

Synonyms:(5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

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Chemical Property of (5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

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Technology Process of (5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

There total 8 articles about (5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene 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: 72.0%

: 188444-27-1
(E)-(S)-8-(4-Chloro-phenylselanyl)-4-mercapto-2,4,6-trimethyl-3-oxo-oct-5-enoic acid methyl ester

: 123402-03-9
(5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

Guidance literature:: With potassium hydroxide; In ethanol;
DOI:10.1039/c39890000023

Reference yield:

: 123401-98-9
Ethyl (2S,3E)-2,4-dimethyl-2-(4-methoxybenzylthio)hexa-3,5-dienoate

: 123402-03-9
(5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) 9-BBN, 2.) 30percent aq. H₂O₂ / 1.) THF, 18 h, 2.) r.t., 45 min

2: 86 percent / Bu₃P / tetrahydrofuran / 0.75 h

3: 99 percent / aq. KOH / ethanol / 3 h / 35 °C

4: 91 percent / tetrahydrofuran / 18 h

5: 61 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C to -30 deg C, 2.5 h

6: 52 percent / Hg(OAc)2, CF₃CO₂H / various solvent(s) / 0.17 h / -20 °C

7: 48 percent / KOH / ethanol / 2.5 h / Ambient temperature

With potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; tributylphosphine; mercury(II) diacetate; dihydrogen peroxide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; ethanol;

Reference yield:

: 123401-96-7
Ethyl (2S,3E)-4-formyl-2-(4-methoxybenzylthio)-2-methylpent-3-enoate

: 123402-03-9
(5S)-5-<(E)-4-(4-Chlorophenylselenenyl)-2-methylbut-1-enyl>-2,5-dihydro-4-hydroxy-3,5-dimethyl-2-oxothiophene

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) BuLi / 1.) THF, hexane, r.t., 1 h, 2.) r.t., 5 h

2: 1.) 9-BBN, 2.) 30percent aq. H₂O₂ / 1.) THF, 18 h, 2.) r.t., 45 min

3: 86 percent / Bu₃P / tetrahydrofuran / 0.75 h

4: 99 percent / aq. KOH / ethanol / 3 h / 35 °C

5: 91 percent / tetrahydrofuran / 18 h

6: 61 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C to -30 deg C, 2.5 h

7: 52 percent / Hg(OAc)2, CF₃CO₂H / various solvent(s) / 0.17 h / -20 °C

8: 48 percent / KOH / ethanol / 2.5 h / Ambient temperature

With potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; tributylphosphine; mercury(II) diacetate; dihydrogen peroxide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; ethanol;