(3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

Base Information

Chemical Name:(3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one
CAS No.:909911-32-6
Molecular Formula:C₁₄H₁₄O₃S
Molecular Weight:262.329
Hs Code.:

Synonyms:(3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

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Chemical Property of (3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

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Technology Process of (3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

There total 6 articles about (3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-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: 76.0%

: 909911-52-0
tert-butyl (1S,2R)-2-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-1-(phenylthio)cyclopent-3-ene-1-carboxylate

: 909911-32-6
(3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

Guidance literature:: With trifluoroacetic acid; at 80 ℃; for 2h;
DOI:10.1021/ol061377y

Reference yield:

: (R)-(S)-3-(1,4-Dioxa-spiro[4.5]dec-2-yl)-pent-4-enoic acid

: 909911-32-6
(3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.49 g / 4-dimethylaminopyridine; 1,3-dicyclohexylcarbodiimide / tetrahydrofuran; CH₂Cl₂ / 16.5 h / 0 - 20 °C

2: 83 percent / LDA; diisopropylamine; HMPA / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

3: 86 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 36 h / 60 °C

4: 77 percent / LDA; HMPA; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 - -30 °C

5: 76 percent / aq. CF₃CO₂H / 2 h / 80 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; Grubbs catalyst first generation; diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1021/ol061377y

Reference yield:

: 909911-49-5
tert-butyl (3R)-3-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]pent-4-enoate

: 909911-32-6
(3R,3aR,6aS)-3-(hydroxymethyl)-6a-(phenylthio)-3,3a,6,6a-tetrahydro-1H-cyclopenta[c]furan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / LDA; diisopropylamine; HMPA / tetrahydrofuran; hexane / 5 h / -78 - 20 °C

2: 86 percent / (PCy₃)2Cl₂Ru=CHPh / benzene / 36 h / 60 °C

3: 77 percent / LDA; HMPA; diisopropylamine / tetrahydrofuran; hexane / 2 h / -78 - -30 °C

4: 76 percent / aq. CF₃CO₂H / 2 h / 80 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; Grubbs catalyst first generation; diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; hexane; benzene;
DOI:10.1021/ol061377y