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

Base Information

Chemical Name:(E)-(S)-8-(4-Chloro-phenylselanyl)-4-mercapto-2,4,6-trimethyl-3-oxo-oct-5-enoic acid methyl ester
CAS No.:188444-27-1
Molecular Formula:C₁₈H₂₃ClO₃SSe
Molecular Weight:433.858
Hs Code.:

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

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Chemical Property of (E)-(S)-8-(4-Chloro-phenylselanyl)-4-mercapto-2,4,6-trimethyl-3-oxo-oct-5-enoic acid methyl ester

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Technology Process of (E)-(S)-8-(4-Chloro-phenylselanyl)-4-mercapto-2,4,6-trimethyl-3-oxo-oct-5-enoic acid methyl ester

There total 7 articles about (E)-(S)-8-(4-Chloro-phenylselanyl)-4-mercapto-2,4,6-trimethyl-3-oxo-oct-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: 58.0%

: 188444-26-0
Methyl (4S,5E)-8-(4-chlorophenylselenenyl)-4-(4-methoxybenzylthio)-2,4,6-trimethyl-3-oxooct-5-enoate

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

Guidance literature:: With hydrogen sulfide; trifluoroacetic acid; mercury (I) acetate;
DOI:10.1039/c39890000023

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

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

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

Guidance literature:: Multi-step reaction with 7 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

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;