methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

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Chemical Name:methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate
CAS No.:774234-66-1
Molecular Formula:C₂₄H₂₃F₃O₄S
Molecular Weight:464.505
Hs Code.:

Synonyms:methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

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Chemical Property of methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

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Technology Process of methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

There total 6 articles about methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate 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: 42.0%

: methyl (2S)-3-hydroxy-3-phenyl-2-[(1R)-2-[(S)-(p-tolylsulfinyl)]-2-cyclopentenyl]propanoate

: 407-25-0
trifluoroacetic anhydride

: 774234-65-0
methyl (2S,3S)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

: 774234-66-1
methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

Guidance literature:: With sodium iodide; In acetone; at 0 ℃; for 0.0833333h;
DOI:10.1021/jo0492923

Reference yield:

: 63268-43-9
(+)-(S)-dimethyl-p-tolylsulfinylmethanephosphonate

: 774234-66-1
methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 33 percent / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.1: 93 percent / p-TsOH*H₂O / methanol / 1 h / 20 °C

3.1: 79 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.67 h / 0 - 20 °C

4.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.25 h / -78 °C

4.2: 87 percent / tetrahydrofuran; toluene / 0.25 h / -78 °C

5.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 0.33 h / -78 °C

5.2: tetrahydrofuran; heptane; ethylbenzene / 0.5 h / 0 °C

6.1: 48 percent / NaI / acetone / 0.08 h / 0 °C

With n-butyllithium; 18-crown-6 ether; potassium hexamethylsilazane; Dess-Martin periodane; toluene-4-sulfonic acid; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; n-heptane; dichloromethane; ethylbenzene; acetone; toluene; 5.1: Michael addition;
DOI:10.1021/jo0492923

Reference yield:

: 311805-03-5
(E)-5-[(R)-(p-tolylsulfinyl)]-4-pentenal

: 774234-66-1
methyl (2S,3R)-3-phenyl-2-[(1R)-2-(p-tolylthio)-2-cyclopentenyl]-3-(2,2,2-trifluoroacetoxy)propanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.25 h / -78 °C

1.2: 87 percent / tetrahydrofuran; toluene / 0.25 h / -78 °C

2.1: LDA / tetrahydrofuran; heptane; ethylbenzene / 0.33 h / -78 °C

2.2: tetrahydrofuran; heptane; ethylbenzene / 0.5 h / 0 °C

3.1: 48 percent / NaI / acetone / 0.08 h / 0 °C

With 18-crown-6 ether; potassium hexamethylsilazane; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; acetone; toluene; 2.1: Michael addition;
DOI:10.1021/jo0492923